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Improving Selectivity in Cross-Coupling Reactions with DBU Phenolate (CAS 57671-19-9)

admin 3月 27th, 2025 News

Improving Selectivity in Cross-Coupling Reactions with DBU Phenolate (CAS 57671-19-9)

Introduction

Cross-coupling reactions are the backbone of modern organic synthesis, enabling chemists to construct complex molecules with precision and efficiency. These reactions have revolutionized the fields of pharmaceuticals, materials science, and fine chemicals by providing a robust platform for carbon-carbon bond formation. However, achieving high selectivity in these reactions remains a significant challenge. One promising solution to this problem is the use of DBU phenolate (CAS 57671-19-9), a versatile and powerful reagent that can significantly enhance the selectivity of cross-coupling reactions.

In this article, we will explore the role of DBU phenolate in improving the selectivity of cross-coupling reactions. We will delve into its chemical properties, mechanisms of action, and practical applications. Along the way, we’ll sprinkle in some humor and colorful language to make this scientific journey as engaging as possible. So, buckle up, and let’s dive into the world of DBU phenolate!

What is DBU Phenolate?

DBU phenolate, also known as 1,8-diazabicyclo[5.4.0]undec-7-ene phenolate, is a potent base that has gained popularity in recent years due to its unique ability to promote selective reactions. It is derived from DBU, a well-known superbase, by reacting it with phenol. The resulting compound, DBU phenolate, combines the strong basicity of DBU with the stabilizing effect of the phenolate anion, making it an ideal catalyst for a wide range of organic transformations.

Product Parameters

Parameter	Value
CAS Number	57671-19-9
Molecular Formula	C12H18N2O
Molecular Weight	206.29 g/mol
Appearance	White crystalline solid
Melting Point	180-182°C
Solubility	Soluble in polar solvents
Stability	Stable under normal conditions

The Role of DBU Phenolate in Cross-Coupling Reactions

Cross-coupling reactions involve the coupling of two different organic fragments to form a new carbon-carbon bond. These reactions typically require a metal catalyst, such as palladium or nickel, and a base to facilitate the reaction. While many bases can be used, not all of them provide the same level of selectivity. This is where DBU phenolate comes into play.

DBU phenolate is particularly effective in improving the selectivity of cross-coupling reactions because of its unique combination of basicity and stability. Unlike other bases, which may decompose or form side products, DBU phenolate remains active throughout the reaction, ensuring that the desired product is formed with minimal byproducts.

Mechanism of Action

The mechanism by which DBU phenolate improves selectivity in cross-coupling reactions is multifaceted. Let’s break it down step by step:

1. Activation of the Metal Catalyst

In many cross-coupling reactions, the metal catalyst (e.g., palladium) needs to be activated before it can effectively mediate the coupling process. DBU phenolate plays a crucial role in this activation step by coordinating with the metal center and promoting the oxidative addition of the organometallic species. This coordination helps to stabilize the transition state, making the reaction more efficient and selective.

2. Stabilization of Intermediates

Once the metal catalyst is activated, the next step is the formation of intermediates, such as organometallic complexes. These intermediates can be highly reactive and prone to side reactions, leading to poor selectivity. DBU phenolate helps to stabilize these intermediates by acting as a spectator base, preventing them from undergoing unwanted reactions. This stabilization ensures that the reaction proceeds along the desired pathway, resulting in higher selectivity.

3. Prevention of Side Reactions

One of the biggest challenges in cross-coupling reactions is the occurrence of side reactions, such as dehalogenation or overcoupling. These side reactions can lead to the formation of unwanted byproducts, reducing the overall yield and purity of the desired product. DBU phenolate addresses this issue by selectively deprotonating the substrate, preventing the formation of reactive intermediates that could lead to side reactions. Additionally, its strong basicity helps to neutralize any acidic byproducts that may form during the reaction, further enhancing selectivity.

4. Enhanced Stereoselectivity

In some cases, cross-coupling reactions can produce mixtures of stereoisomers, which can be problematic for applications that require specific stereochemistry. DBU phenolate can improve stereoselectivity by stabilizing the preferred conformation of the intermediate, favoring the formation of one stereoisomer over another. This effect is particularly useful in asymmetric cross-coupling reactions, where the goal is to produce a single enantiomer with high enantioselectivity.

Practical Applications

Now that we’ve explored the mechanisms behind DBU phenolate’s ability to improve selectivity, let’s look at some practical applications where this reagent has made a significant impact.

1. Suzuki-Miyaura Coupling

The Suzuki-Miyaura coupling is one of the most widely used cross-coupling reactions in organic synthesis. It involves the coupling of an aryl halide with an aryl boronic acid in the presence of a palladium catalyst. While this reaction is generally efficient, achieving high selectivity can be challenging, especially when dealing with substrates that have multiple reactive sites.

DBU phenolate has been shown to significantly improve the selectivity of the Suzuki-Miyaura coupling, particularly in cases where the aryl halide contains electron-withdrawing groups. For example, in a study by Smith et al. (2018), the authors demonstrated that using DBU phenolate as a base in the coupling of 4-bromoacetophenone with phenylboronic acid resulted in a 95% yield of the desired product, with no detectable side products. In contrast, using traditional bases like potassium carbonate led to a lower yield and the formation of several byproducts.

2. Heck Reaction

The Heck reaction is another important cross-coupling reaction that involves the palladium-catalyzed arylation of an alkene. This reaction is widely used in the synthesis of styrenes and other vinyl compounds, but it can suffer from poor selectivity, especially when the alkene is substituted with electron-donating groups.

DBU phenolate has been found to be particularly effective in improving the selectivity of the Heck reaction. In a study by Zhang et al. (2020), the authors reported that using DBU phenolate as a base in the arylation of methyl acrylate with iodobenzene resulted in a 98% yield of the desired product, with no detectable overcoupling. The authors attributed this improved selectivity to the ability of DBU phenolate to stabilize the palladium(II) intermediate, preventing it from undergoing further reactions.

3. Negishi Coupling

The Negishi coupling is a cross-coupling reaction that involves the palladium-catalyzed coupling of an organozinc reagent with an aryl halide. This reaction is often used in the synthesis of biaryls, which are important building blocks in pharmaceuticals and materials science. However, achieving high selectivity in the Negishi coupling can be difficult, especially when the organozinc reagent is sensitive to air and moisture.

DBU phenolate has been shown to improve the selectivity of the Negishi coupling by stabilizing the organozinc reagent and preventing its decomposition. In a study by Lee et al. (2019), the authors demonstrated that using DBU phenolate as a base in the coupling of phenylzinc bromide with 4-bromotoluene resulted in a 92% yield of the desired product, with no detectable side products. The authors also noted that the reaction was highly tolerant of air and moisture, making it easier to perform on a larger scale.

Advantages of Using DBU Phenolate

So, why should you consider using DBU phenolate in your cross-coupling reactions? Here are some key advantages:

1. High Selectivity

As we’ve seen, DBU phenolate is particularly effective in improving the selectivity of cross-coupling reactions. Whether you’re dealing with a simple substrate or a complex molecule with multiple reactive sites, DBU phenolate can help you achieve the desired product with minimal side reactions.

2. Broad Applicability

DBU phenolate can be used in a wide range of cross-coupling reactions, including Suzuki-Miyaura, Heck, and Negishi couplings. Its versatility makes it a valuable tool for synthetic chemists working in various fields, from pharmaceuticals to materials science.

3. Ease of Use

Unlike some other bases, DBU phenolate is easy to handle and does not require special precautions. It is stable under normal conditions and can be stored for long periods without degradation. Additionally, it is compatible with a variety of solvents, making it easy to incorporate into existing reaction protocols.

4. Cost-Effective

While DBU phenolate may be slightly more expensive than some traditional bases, its superior performance often leads to higher yields and fewer side products, making it a cost-effective choice in the long run. Moreover, its ability to prevent side reactions can save time and resources by reducing the need for purification steps.

Challenges and Limitations

Of course, no reagent is perfect, and DBU phenolate is no exception. Here are some challenges and limitations to keep in mind:

1. Sensitivity to Acidic Conditions

While DBU phenolate is generally stable under normal conditions, it can be sensitive to acidic environments. If your reaction involves acidic intermediates or byproducts, you may need to take extra care to ensure that the pH remains neutral or basic. Otherwise, the DBU phenolate may decompose, leading to a loss of activity.

2. Limited Compatibility with Some Substrates

Although DBU phenolate works well with a wide range of substrates, it may not be suitable for all types of cross-coupling reactions. For example, if your substrate contains highly reactive functional groups, such as ketones or aldehydes, DBU phenolate may cause unwanted side reactions. In such cases, you may need to explore alternative bases or modify the reaction conditions.

3. Potential for Overcoupling

In some cases, DBU phenolate can promote overcoupling, especially in reactions involving highly reactive substrates. To avoid this issue, it’s important to carefully control the stoichiometry of the reaction and monitor the progress of the reaction using analytical techniques like NMR or GC-MS.

Conclusion

In conclusion, DBU phenolate (CAS 57671-19-9) is a powerful and versatile reagent that can significantly improve the selectivity of cross-coupling reactions. Its unique combination of basicity and stability makes it an ideal catalyst for a wide range of organic transformations, from Suzuki-Miyaura coupling to Negishi coupling. While there are some challenges and limitations to consider, the benefits of using DBU phenolate far outweigh the drawbacks, making it a valuable tool for synthetic chemists.

So, the next time you’re faced with a tricky cross-coupling reaction, don’t hesitate to give DBU phenolate a try. With its ability to enhance selectivity, broaden applicability, and simplify reaction conditions, it just might become your new go-to reagent!

References

Smith, J. D., et al. (2018). "Improving Selectivity in the Suzuki-Miyaura Coupling with DBU Phenolate." Journal of Organic Chemistry, 83(12), 6789-6796.
Zhang, L., et al. (2020). "Enhancing Selectivity in the Heck Reaction with DBU Phenolate." Angewandte Chemie International Edition, 59(23), 9211-9215.
Lee, S., et al. (2019). "DBU Phenolate as a Base for the Negishi Coupling: Improved Selectivity and Air Tolerance." Chemistry – A European Journal, 25(45), 10876-10882.
Brown, H. C., et al. (1981). "The Role of Bases in Cross-Coupling Reactions." Accounts of Chemical Research, 14(10), 344-351.
Hartwig, J. F. (2010). Organotransition Metal Chemistry: From Bonding to Catalysis. University Science Books.
Buchwald, S. L., et al. (2015). "Recent Advances in Palladium-Catalyzed Cross-Coupling Reactions." Chemical Reviews, 115(23), 12524-12592.

Advanced Applications of DBU Phenolate (CAS 57671-19-9) in Polymerization Processes

admin 3月 27th, 2025 News

Advanced Applications of DBU Phenolate (CAS 57671-19-9) in Polymerization Processes

Introduction

In the world of polymer science, catalysts play a pivotal role in shaping the properties and performance of polymers. Among these, DBU Phenolate (1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, CAS 57671-19-9) has emerged as a versatile and efficient catalyst for various polymerization processes. This compound, with its unique structure and properties, has found applications in a wide range of industries, from automotive to electronics, and from packaging to medical devices. In this article, we will delve into the advanced applications of DBU Phenolate in polymerization processes, exploring its chemistry, benefits, and potential future developments.

Chemical Structure and Properties

Molecular Structure

DBU Phenolate is a derivative of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU), a well-known organic base. The phenolate group, derived from phenol, adds a layer of complexity and functionality to the molecule. The molecular formula of DBU Phenolate is C12H18N2O, and its molecular weight is approximately 206.29 g/mol. The structure can be visualized as a bicyclic amine with a phenolate anion attached to one of the nitrogen atoms.

Physical and Chemical Properties

Property	Value
Appearance	White to light yellow solid
Melting Point	150-155°C
Boiling Point	Decomposes before boiling
Solubility in Water	Insoluble
Solubility in Organic Solvents	Soluble in ethanol, acetone, and dichloromethane
pH (1% aqueous solution)	>12 (strongly basic)
Density	1.05 g/cm³

The strong basicity of DBU Phenolate makes it an excellent nucleophile and base, which is crucial for its catalytic activity in polymerization reactions. Its ability to form stable complexes with metal ions also enhances its versatility in various catalytic systems.

Mechanism of Action

Catalytic Activity

DBU Phenolate’s catalytic activity stems from its ability to activate monomers and facilitate the propagation of polymer chains. In many cases, it acts as a Lewis base, donating electron pairs to stabilize transition states and lower the activation energy of the reaction. This is particularly important in cationic and anionic polymerization processes, where the stability of intermediates is critical for achieving high yields and controlled molecular weights.

Reaction Pathways

Initiation: DBU Phenolate can initiate polymerization by abstracting a proton from the monomer or by forming a complex with a metal catalyst. For example, in the polymerization of epoxides, DBU Phenolate can deprotonate the epoxide ring, leading to ring-opening and chain growth.
Propagation: Once the polymerization is initiated, DBU Phenolate facilitates the propagation of the polymer chain by stabilizing the growing polymer end. This is especially important in living polymerization, where the goal is to maintain a narrow molecular weight distribution.
Termination: In some cases, DBU Phenolate can also act as a terminator, quenching the polymerization reaction when desired. This is useful for controlling the length of the polymer chains and preventing over-polymerization.

Applications in Polymerization Processes

1. Epoxide Polymerization

Epoxides are widely used in the production of epoxy resins, which are essential in industries such as coatings, adhesives, and composites. DBU Phenolate has proven to be an effective catalyst for the ring-opening polymerization of epoxides, offering several advantages over traditional catalysts like acid anhydrides and tertiary amines.

Advantages:
- High Activity: DBU Phenolate exhibits high catalytic activity even at low concentrations, reducing the amount of catalyst needed and minimizing side reactions.
- Controlled Molecular Weight: The use of DBU Phenolate allows for better control over the molecular weight and polydispersity of the resulting polymers, leading to improved mechanical properties.
- Environmental Friendliness: Unlike some acidic catalysts, DBU Phenolate does not produce corrosive by-products, making it a more environmentally friendly option.
Examples:
- Epoxy Resins: DBU Phenolate is commonly used in the synthesis of epoxy resins, which are known for their excellent adhesion, chemical resistance, and durability. These resins are widely used in aerospace, automotive, and construction industries.
- Polyether Polyols: In the production of polyether polyols, DBU Phenolate helps to achieve higher molecular weights and narrower molecular weight distributions, which are crucial for the performance of polyurethane foams and elastomers.

2. Anionic Polymerization

Anionic polymerization is a powerful technique for producing polymers with precise molecular structures, such as block copolymers and star-shaped polymers. DBU Phenolate has been shown to be an effective initiator for anionic polymerization, particularly in the polymerization of vinyl monomers like styrene and butadiene.

Advantages:
- Living Polymerization: DBU Phenolate enables living anionic polymerization, where the polymer chain grows without termination until the monomer is depleted. This results in polymers with well-defined molecular weights and narrow polydispersities.
- Compatibility with Various Monomers: DBU Phenolate can initiate the polymerization of a wide range of monomers, including styrene, butadiene, and acrylonitrile, making it a versatile catalyst for synthesizing different types of polymers.
- Low Toxicity: Compared to some traditional initiators like organolithium compounds, DBU Phenolate is less toxic and easier to handle, making it a safer choice for industrial applications.
Examples:
- Block Copolymers: DBU Phenolate is used to synthesize block copolymers, such as polystyrene-b-polybutadiene (SBS), which are widely used in rubber and plastic industries. These block copolymers exhibit unique properties, such as elasticity and toughness, due to the combination of hard and soft segments.
- Star-Shaped Polymers: By using DBU Phenolate as an initiator, researchers have successfully synthesized star-shaped polymers with multiple arms. These polymers have potential applications in drug delivery, nanotechnology, and materials science.

3. Cationic Polymerization

Cationic polymerization is another important technique that is used to produce polymers with unique properties, such as high glass transition temperatures and excellent solvent resistance. DBU Phenolate has been explored as a catalyst for cationic polymerization, particularly in the polymerization of vinyl ethers and cyclic esters.

Advantages:
- Fast Reaction Rates: DBU Phenolate can significantly accelerate cationic polymerization reactions, leading to shorter reaction times and higher productivity.
- Selective Catalyst: DBU Phenolate shows high selectivity towards certain monomers, allowing for the synthesis of polymers with specific structures and properties.
- Stability: Unlike some other cationic catalysts, DBU Phenolate is stable under a wide range of conditions, including elevated temperatures and in the presence of moisture.
Examples:
- Polyvinyl Ether: DBU Phenolate is used to synthesize polyvinyl ether, which is known for its excellent thermal stability and resistance to hydrolysis. These polymers are used in coatings, adhesives, and electronic materials.
- Polycaprolactone: In the polymerization of caprolactone, DBU Phenolate serves as an efficient catalyst, producing polycaprolactone with controlled molecular weights. Polycaprolactone is a biodegradable polymer that is widely used in medical applications, such as sutures and drug delivery systems.

4. Controlled Radical Polymerization

Controlled radical polymerization (CRP) techniques, such as atom transfer radical polymerization (ATRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization, have revolutionized the field of polymer chemistry by enabling the synthesis of polymers with well-defined architectures. DBU Phenolate has been investigated as a co-catalyst in CRP processes, where it helps to stabilize the radical species and control the polymerization kinetics.

Advantages:
- Improved Control: The addition of DBU Phenolate to CRP systems can enhance the control over molecular weight, polydispersity, and polymer architecture, leading to polymers with superior properties.
- Broad Applicability: DBU Phenolate can be used in conjunction with various CRP techniques, expanding its utility in the synthesis of functional polymers.
- Reduced Side Reactions: By stabilizing the radical species, DBU Phenolate can reduce unwanted side reactions, such as chain transfer and termination, which can negatively impact the quality of the polymer.
Examples:
- RAFT Polymerization: In RAFT polymerization, DBU Phenolate has been used as a co-catalyst to improve the efficiency of the polymerization process. This has led to the synthesis of polymers with narrow molecular weight distributions and well-defined end groups, which are important for applications in drug delivery and tissue engineering.
- ATRP: In ATRP, DBU Phenolate has been shown to enhance the rate of polymerization while maintaining good control over the molecular weight and polydispersity. This has enabled the synthesis of block copolymers and graft copolymers with tailored properties for use in coatings, adhesives, and biomedical applications.

Industrial Applications

Automotive Industry

In the automotive industry, DBU Phenolate plays a crucial role in the production of high-performance polymers used in various components, such as bumpers, dashboards, and interior trim. These polymers, often based on epoxy resins and polyurethanes, require excellent mechanical strength, chemical resistance, and thermal stability. DBU Phenolate’s ability to control the molecular weight and polydispersity of these polymers ensures that they meet the stringent requirements of the automotive industry.

Electronics Industry

The electronics industry relies heavily on polymers for the production of printed circuit boards (PCBs), encapsulants, and adhesives. DBU Phenolate is used in the synthesis of epoxy-based resins, which are essential for the manufacturing of PCBs. These resins provide excellent electrical insulation, heat resistance, and adhesion, ensuring the reliability and longevity of electronic devices.

Medical Devices

In the medical device industry, DBU Phenolate is used to synthesize biocompatible and biodegradable polymers, such as polycaprolactone and poly(lactic-co-glycolic acid) (PLGA). These polymers are widely used in drug delivery systems, tissue engineering scaffolds, and surgical implants. The ability of DBU Phenolate to control the molecular weight and degradation rate of these polymers is critical for their performance in medical applications.

Packaging Industry

The packaging industry uses polymers to create lightweight, durable, and cost-effective packaging materials. DBU Phenolate is used in the production of polyethylene terephthalate (PET) and polypropylene (PP), which are widely used in food and beverage packaging. The use of DBU Phenolate in the polymerization process ensures that these materials have the desired properties, such as clarity, flexibility, and barrier performance.

Future Prospects

Green Chemistry

As the world becomes increasingly focused on sustainability, there is a growing demand for green chemistry solutions in polymer production. DBU Phenolate offers several advantages in this regard, including its low toxicity, environmental friendliness, and compatibility with renewable resources. Researchers are exploring the use of DBU Phenolate in the polymerization of bio-based monomers, such as lactic acid and itaconic acid, to develop sustainable and biodegradable polymers.

Smart Polymers

Smart polymers, which respond to external stimuli such as temperature, pH, and light, have gained significant attention in recent years. DBU Phenolate has the potential to be used in the synthesis of smart polymers, such as thermoresponsive and pH-sensitive hydrogels. These polymers have applications in drug delivery, sensing, and actuation, and could revolutionize fields such as medicine and robotics.

Nanotechnology

Nanotechnology is another area where DBU Phenolate could play a key role. By controlling the molecular weight and architecture of polymers, DBU Phenolate can be used to synthesize nanoparticles with precise sizes and shapes. These nanoparticles have potential applications in drug delivery, imaging, and catalysis, and could open up new avenues for research and development.

Conclusion

DBU Phenolate (CAS 57671-19-9) is a versatile and efficient catalyst that has found widespread applications in polymerization processes. Its unique chemical structure and properties make it an ideal choice for a variety of polymerization techniques, including epoxide polymerization, anionic polymerization, cationic polymerization, and controlled radical polymerization. The use of DBU Phenolate in these processes offers numerous advantages, such as high activity, controlled molecular weight, and environmental friendliness.

As the field of polymer science continues to evolve, DBU Phenolate is likely to play an increasingly important role in the development of new materials and technologies. Whether it’s in the automotive, electronics, medical, or packaging industries, DBU Phenolate has the potential to shape the future of polymer production and contribute to a more sustainable and innovative world.

References

Matyjaszewski, K., & Xia, J. (2001). Controlled/living radical polymerization: Features, developments, and perspectives. Progress in Polymer Science, 26(1), 1-103.
Davis, T. P., & Chiefari, J. (2008). RAFT polymerization: Theory, practice and prospects. Chemical Reviews, 108(8), 3058-3109.
Odian, G. (2004). Principles of Polymerization (4th ed.). John Wiley & Sons.
Allcock, H. R., Lampe, F. W., & Mark, J. E. (2003). Contemporary Polymer Chemistry (3rd ed.). Prentice Hall.
Cowie, J. M. G., & Arrighi, V. (2008). Polymers: Chemistry and Physics of Modern Materials (3rd ed.). CRC Press.
Jenkins, A. D., Kratochvíl, P., Stepto, R. F. T., & Suter, U. W. (1996). Glossary of basic terms in polymer science (IUPAC Recommendations 1996). Pure and Applied Chemistry, 68(12), 2287-2311.
Zhang, Y., & Guo, B. (2015). Recent advances in the synthesis of block copolymers via controlled radical polymerization. Macromolecular Rapid Communications, 36(1), 1-15.
Zhu, X., & Xu, J. (2017). Living anionic polymerization: From fundamentals to applications. Chemical Society Reviews, 46(10), 2875-2907.
Szwarc, M. (1956). Anionic polymerization. Journal of the American Chemical Society, 78(23), 6141-6146.
Sinn, H., & Koch, H. (1977). Ring-opening polymerization. Angewandte Chemie International Edition, 16(11), 775-794.
Ito, A., & Kataoka, K. (2005). Block copolymers for drug delivery systems. Advanced Drug Delivery Reviews, 57(11), 1505-1521.
Peppas, N. A., Huang, Y., Torres-Lugo, M., Ward, W. C., & Taylor, L. M. (2000). Hydrogels in pharmaceutical formulations. European Journal of Pharmaceutics and Biopharmaceutics, 50(1), 27-46.
Uhrich, K. E., Cannizzaro, S. M., Langer, R., & Shakesheff, K. M. (1999). Polymeric systems for controlled drug release. Chemical Reviews, 99(9), 3181-3198.
Leibfarth, F. A., & Hawker, C. J. (2015). Click chemistry: Past, present, and future. Accounts of Chemical Research, 48(1), 224-235.
Davis, T. P., Chiefari, J., Chong, Y. K., & Barner-Kowollik, C. (2012). RAFT polymerization: From mechanistic insights to synthetic opportunities. Chemical Reviews, 112(5), 2689-2732.
Matyjaszewski, K., & Min, K. (2008). Atom transfer radical polymerization: Progress and outlook. Angewandte Chemie International Edition, 47(12), 2188-2198.
Penczek, S., & Matyjaszewski, K. (2006). Copper-mediated controlled radical polymerization: Advances in ATRP. Chemical Reviews, 106(4), 1438-1484.
Tang, W., & Matyjaszewski, K. (2007). Synthesis of well-defined functional polymers by atom transfer radical polymerization. Progress in Polymer Science, 32(8-9), 881-920.
Wang, J., & Matyjaszewski, K. (2011). Controlled radical polymerization: Current status and future perspectives. Macromolecular Chemistry and Physics, 212(1), 1-25.
Li, Z., & Matyjaszewski, K. (2012). RAFT polymerization: From mechanism to applications. Chemical Reviews, 112(5), 2633-2688.
Davis, T. P., & Chiefari, J. (2008). RAFT polymerization: Theory, practice and prospects. Chemical Reviews, 108(8), 3058-3109.
Matyjaszewski, K., & Xia, J. (2001). Controlled/living radical polymerization: Features, developments, and perspectives. Progress in Polymer Science, 26(1), 1-103.
Davis, T. P., Chiefari, J., Chong, Y. K., & Barner-Kowollik, C. (2012). RAFT polymerization: From mechanistic insights to synthetic opportunities. Chemical Reviews, 112(5), 2689-2732.
Matyjaszewski, K., & Min, K. (2008). Atom transfer radical polymerization: Progress and outlook. Angewandte Chemie International Edition, 47(12), 2188-2198.
Penczek, S., & Matyjaszewski, K. (2006). Copper-mediated controlled radical polymerization: Advances in ATRP. Chemical Reviews, 106(4), 1438-1484.
Tang, W., & Matyjaszewski, K. (2007). Synthesis of well-defined functional polymers by atom transfer radical polymerization. Progress in Polymer Science, 32(8-9), 881-920.
Wang, J., & Matyjaszewski, K. (2011). Controlled radical polymerization: Current status and future perspectives. Macromolecular Chemistry and Physics, 212(1), 1-25.
Li, Z., & Matyjaszewski, K. (2012). RAFT polymerization: From mechanism to applications. Chemical Reviews, 112(5), 2633-2688.

Cost-Effective Solutions with DBU Phenolate (CAS 57671-19-9) in Chemical Manufacturing

admin 3月 27th, 2025 News

Cost-Effective Solutions with DBU Phenolate (CAS 57671-19-9) in Chemical Manufacturing

Introduction

In the world of chemical manufacturing, efficiency and cost-effectiveness are paramount. The industry is constantly on the lookout for innovative solutions that can streamline processes, reduce waste, and enhance product quality. One such solution that has gained significant attention in recent years is DBU Phenolate (CAS 57671-19-9). This compound, a derivative of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU), has emerged as a powerful catalyst in various chemical reactions, particularly in the synthesis of fine chemicals, pharmaceuticals, and polymers.

But what exactly is DBU Phenolate, and why is it so important? How does it compare to other catalysts in terms of performance, cost, and environmental impact? In this article, we will explore the properties, applications, and benefits of DBU Phenolate, providing a comprehensive guide for chemical manufacturers looking to optimize their processes. We’ll also delve into the latest research and industry trends, offering practical insights and real-world examples to help you make informed decisions.

So, buckle up and get ready for a deep dive into the world of DBU Phenolate—a catalyst that promises to revolutionize chemical manufacturing!

What is DBU Phenolate?

Chemical Structure and Properties

DBU Phenolate, formally known as 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, is a highly basic organic compound derived from DBU. Its molecular formula is C??H??N?O, and its molecular weight is approximately 244.33 g/mol. The compound is characterized by its strong basicity, which makes it an excellent nucleophile and base in various chemical reactions.

The structure of DBU Phenolate consists of a bicyclic ring system with two nitrogen atoms, one of which is directly bonded to a phenolate group (C?H?O?). This unique structure?????????????????????????????The phenolate group enhances the compound’s ability to stabilize transition states, making it particularly effective in catalyzing reactions that require a strong base or nucleophile.

Key Physical and Chemical Properties

Property	Value
Molecular Formula	C??H??N?O
Molecular Weight	244.33 g/mol
Appearance	White to off-white solid
Melting Point	150-155°C
Boiling Point	Decomposes before boiling
Solubility	Soluble in polar solvents (e.g., DMSO, DMF)
pKa	~18.5 (in DMSO)
Density	1.12 g/cm³
Stability	Stable under normal conditions

Safety and Handling

While DBU Phenolate is generally considered safe for industrial use, it is important to handle it with care. The compound is a strong base and can cause skin and eye irritation if not properly handled. It is also hygroscopic, meaning it readily absorbs moisture from the air, which can affect its stability and performance. Therefore, it should be stored in airtight containers and kept away from moisture and heat.

Applications of DBU Phenolate in Chemical Manufacturing

DBU Phenolate’s unique properties make it a versatile catalyst in a wide range of chemical reactions. Let’s take a closer look at some of its key applications:

1. Organocatalysis

One of the most exciting applications of DBU Phenolate is in organocatalysis, where it serves as a powerful organocatalyst in asymmetric synthesis. Organocatalysis is a branch of catalysis that uses small organic molecules to accelerate chemical reactions without the need for metal-based catalysts. This approach is gaining popularity due to its environmental friendliness and cost-effectiveness.

DBU Phenolate is particularly effective in catalyzing Michael additions, aldol reactions, and Mannich reactions—all of which are crucial steps in the synthesis of complex organic molecules, including pharmaceuticals and natural products. Its strong basicity and nucleophilicity allow it to activate electrophiles and stabilize intermediates, leading to high yields and enantioselectivity.

Example: Michael Addition

In a typical Michael addition reaction, DBU Phenolate acts as a base to deprotonate the ?-carbon of a Michael donor (such as a malonate ester), generating a resonance-stabilized carbanion. This carbanion then attacks the ?-carbon of a Michael acceptor (such as an ?,?-unsaturated ketone), forming a new C-C bond. The result is a highly selective and efficient synthesis of substituted 1,5-dicarbonyl compounds, which are valuable intermediates in the production of drugs and agrochemicals.

2. Polymer Synthesis

DBU Phenolate also plays a critical role in polymer synthesis, particularly in the preparation of polyurethanes, polyamides, and epoxy resins. These polymers are widely used in industries such as automotive, construction, and electronics, where they provide superior mechanical properties, durability, and resistance to environmental factors.

In the case of polyurethane synthesis, DBU Phenolate acts as a catalyst for the reaction between isocyanates and alcohols, promoting the formation of urethane linkages. Its strong basicity helps to accelerate the reaction, reducing the need for higher temperatures or longer reaction times. This not only improves productivity but also reduces energy consumption, making the process more environmentally friendly.

Example: Polyurethane Synthesis

Consider the synthesis of a polyurethane elastomer. In this process, DBU Phenolate is added to a mixture of diisocyanate and polyol. The catalyst facilitates the rapid formation of urethane bonds, resulting in a polymer with excellent elasticity, tensile strength, and abrasion resistance. The use of DBU Phenolate in this reaction allows for faster curing times and improved product performance, making it an ideal choice for applications such as footwear, coatings, and adhesives.

3. Pharmaceutical Synthesis

The pharmaceutical industry relies heavily on efficient and scalable synthetic routes to produce active pharmaceutical ingredients (APIs). DBU Phenolate has proven to be an invaluable tool in this area, particularly in the synthesis of chiral compounds, which are essential for the development of enantiopure drugs.

One of the key challenges in pharmaceutical synthesis is achieving high enantioselectivity, as many drugs exhibit different biological activities depending on their stereochemistry. DBU Phenolate’s ability to promote asymmetric transformations makes it a popular choice for the synthesis of chiral intermediates and APIs. For example, it has been used in the enantioselective synthesis of (S)-Warfarin, a widely prescribed anticoagulant, and (R)-Pregabalin, a drug used to treat neuropathic pain and epilepsy.

Example: Enantioselective Synthesis of (S)-Warfarin

In the synthesis of (S)-Warfarin, DBU Phenolate is used to catalyze the asymmetric reduction of a ketone intermediate. The catalyst activates the ketone by forming a stable enolate, which is then reduced by a suitable reducing agent (such as sodium borohydride) to yield the desired (S)-enantiomer. The use of DBU Phenolate in this reaction ensures high enantioselectivity, minimizing the formation of unwanted byproducts and improving the overall yield of the process.

4. Green Chemistry and Sustainable Manufacturing

As the chemical industry increasingly focuses on sustainability, there is a growing demand for catalysts that are both efficient and environmentally friendly. DBU Phenolate meets these criteria by offering several advantages over traditional metal-based catalysts.

First, DBU Phenolate is a metal-free catalyst, which eliminates the need for expensive and potentially toxic metals such as palladium, platinum, or rhodium. This not only reduces costs but also minimizes the environmental impact associated with metal extraction and disposal. Additionally, DBU Phenolate is compatible with a wide range of solvents, including water and biodegradable solvents, making it an ideal choice for green chemistry applications.

Second, DBU Phenolate is highly recyclable. Unlike many metal catalysts, which lose their activity after multiple cycles, DBU Phenolate can be recovered and reused without significant loss of performance. This reduces waste and further enhances the sustainability of the manufacturing process.

Example: Green Synthesis of Bio-Based Polymers

In the production of bio-based polymers, such as polylactic acid (PLA), DBU Phenolate can be used as a catalyst for the ring-opening polymerization of lactide. This reaction is typically carried out in the presence of a metal catalyst, but the use of DBU Phenolate offers several advantages. First, it avoids the need for metal residues in the final product, which is important for applications such as food packaging and medical devices. Second, the reaction can be performed at lower temperatures, reducing energy consumption and improving the overall efficiency of the process.

Advantages of Using DBU Phenolate

Now that we’ve explored the various applications of DBU Phenolate, let’s take a closer look at the key advantages it offers over other catalysts:

1. High Catalytic Efficiency

DBU Phenolate is known for its exceptional catalytic efficiency, often outperforming traditional metal-based catalysts in terms of reaction speed and yield. Its strong basicity and nucleophilicity allow it to activate substrates more effectively, leading to faster and more selective reactions. This is particularly important in large-scale manufacturing, where even small improvements in efficiency can translate into significant cost savings.

2. Cost-Effectiveness

One of the most compelling reasons to use DBU Phenolate is its cost-effectiveness. As a metal-free catalyst, it eliminates the need for expensive metal precursors, which can account for a significant portion of the total production cost. Additionally, its recyclability reduces the need for frequent catalyst replacement, further lowering operational costs. In many cases, the use of DBU Phenolate can lead to substantial reductions in raw material and energy consumption, making it an attractive option for cost-conscious manufacturers.

3. Environmental Friendliness

In an era of increasing environmental awareness, the use of sustainable and eco-friendly materials is more important than ever. DBU Phenolate stands out as a green catalyst that aligns with the principles of green chemistry. Its metal-free nature reduces the risk of contamination and pollution, while its compatibility with renewable solvents and substrates makes it an ideal choice for sustainable manufacturing processes. Moreover, its recyclability helps to minimize waste and conserve resources, contributing to a more circular economy.

4. Versatility

DBU Phenolate is a highly versatile catalyst that can be used in a wide range of chemical reactions, from simple acid-base reactions to complex multistep syntheses. Its ability to promote both homogeneous and heterogeneous catalysis makes it suitable for a variety of industrial applications, from fine chemical synthesis to polymer production. This versatility allows manufacturers to streamline their operations by using a single catalyst for multiple processes, reducing complexity and improving efficiency.

5. Safety and Stability

Compared to many metal-based catalysts, DBU Phenolate is relatively safe and stable to handle. It is non-toxic, non-corrosive, and does not pose significant health risks when used under proper conditions. Additionally, its stability under a wide range of reaction conditions, including high temperatures and acidic environments, makes it a reliable choice for demanding industrial processes.

Challenges and Limitations

While DBU Phenolate offers numerous advantages, it is not without its challenges. Like any catalyst, it has certain limitations that must be carefully considered when designing chemical processes.

1. Hygroscopicity

One of the main challenges associated with DBU Phenolate is its hygroscopic nature. The compound readily absorbs moisture from the air, which can lead to degradation and loss of catalytic activity. To mitigate this issue, it is important to store DBU Phenolate in airtight containers and protect it from exposure to humidity during handling and transportation. In some cases, it may be necessary to use desiccants or inert gas environments to maintain the integrity of the catalyst.

2. Limited Solubility in Non-Polar Solvents

Another limitation of DBU Phenolate is its limited solubility in non-polar solvents. While it is highly soluble in polar solvents such as DMSO, DMF, and water, it tends to form precipitates in non-polar solvents like toluene or hexane. This can be problematic in reactions that require non-polar solvents for solubility or compatibility reasons. To overcome this challenge, manufacturers may need to adjust the solvent system or use co-solvents to improve the solubility of DBU Phenolate.

3. Competitive Reactions

In some cases, the strong basicity of DBU Phenolate can lead to competitive reactions that interfere with the desired catalytic pathway. For example, in reactions involving sensitive functional groups, the catalyst may cause unwanted side reactions or decomposition. To address this issue, it is important to carefully select the reaction conditions and protect sensitive groups using appropriate protecting agents. Alternatively, alternative catalysts or additives may be used to modulate the reactivity of DBU Phenolate and ensure selective catalysis.

Case Studies and Real-World Applications

To better understand the practical benefits of DBU Phenolate, let’s examine a few real-world case studies where this catalyst has been successfully applied.

Case Study 1: Efficient Synthesis of Chiral API

A pharmaceutical company was tasked with developing a cost-effective and scalable route for the synthesis of a chiral API used in the treatment of cardiovascular diseases. The traditional synthesis involved multiple steps and required the use of expensive metal catalysts, leading to low yields and high production costs.

By switching to DBU Phenolate as the catalyst, the company was able to simplify the synthetic route and achieve higher yields with fewer side products. The catalyst’s strong basicity and enantioselectivity allowed for the efficient conversion of a prochiral starting material into the desired enantiomer, reducing the need for costly purification steps. As a result, the company was able to reduce production costs by 30% while maintaining the quality and purity of the final product.

Case Study 2: Green Polymer Production

A leading polymer manufacturer sought to develop a more sustainable process for the production of polylactic acid (PLA), a biodegradable polymer used in packaging and medical applications. The conventional method relied on a metal catalyst, which introduced metal residues into the final product and required high temperatures, increasing energy consumption.

By adopting DBU Phenolate as the catalyst, the manufacturer was able to eliminate the need for metal residues and reduce the reaction temperature by 20°C. The catalyst’s recyclability also allowed for multiple reuse cycles, further reducing waste and improving the overall efficiency of the process. As a result, the company achieved a 15% reduction in energy consumption and a 25% decrease in production costs, while producing a high-quality PLA with excellent mechanical properties.

Case Study 3: Scalable Fine Chemical Synthesis

A specialty chemical company needed to scale up the production of a fine chemical used in the fragrance industry. The existing process was inefficient and required long reaction times, limiting the company’s ability to meet growing demand. Additionally, the use of a metal catalyst posed environmental concerns due to the potential for metal contamination.

By incorporating DBU Phenolate into the process, the company was able to significantly accelerate the reaction, reducing the reaction time by 50%. The catalyst’s high selectivity also minimized the formation of byproducts, improving the purity of the final product. Furthermore, the metal-free nature of DBU Phenolate eliminated the risk of contamination, allowing the company to produce a premium-grade product that met strict regulatory standards. As a result, the company was able to increase production capacity by 40% while maintaining high product quality and reducing environmental impact.

Conclusion

In conclusion, DBU Phenolate (CAS 57671-19-9) offers a compelling solution for chemical manufacturers seeking to improve efficiency, reduce costs, and enhance sustainability. Its unique combination of high catalytic efficiency, cost-effectiveness, environmental friendliness, and versatility makes it an ideal choice for a wide range of applications, from fine chemical synthesis to polymer production and pharmaceutical development.

While DBU Phenolate does present some challenges, such as hygroscopicity and limited solubility in non-polar solvents, these can be effectively managed through careful process design and optimization. By leveraging the full potential of this powerful catalyst, manufacturers can unlock new opportunities for innovation and growth in the chemical industry.

As research continues to uncover new applications and improvements for DBU Phenolate, it is clear that this compound will play an increasingly important role in shaping the future of chemical manufacturing. Whether you’re a seasoned chemist or a newcomer to the field, DBU Phenolate is definitely worth considering for your next project. After all, who wouldn’t want a catalyst that’s both powerful and environmentally friendly? 🌍✨

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