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Enhancing Reaction Efficiency with DBU Formate (CAS 51301-55-4) in Industrial Processes

3月 27th, 2025 News

Enhancing Reaction Efficiency with DBU Formate (CAS 51301-55-4) in Industrial Processes

Introduction

In the world of industrial chemistry, efficiency is the holy grail. Whether you’re synthesizing pharmaceuticals, producing polymers, or refining petrochemicals, every second and every molecule counts. One compound that has emerged as a game-changer in this quest for efficiency is DBU Formate (CAS 51301-55-4). This versatile reagent, often overlooked in favor of more traditional catalysts, has the potential to revolutionize a wide range of chemical processes. In this article, we’ll dive deep into the world of DBU Formate, exploring its properties, applications, and how it can be harnessed to boost reaction efficiency. So, buckle up, and let’s embark on this chemical journey!

What is DBU Formate?

DBU Formate, formally known as 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, is a derivative of the well-known base DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene). It belongs to the family of organic compounds known as formates, which are salts or esters of formic acid. The addition of the formate group to DBU imparts unique properties that make it particularly useful in catalysis and organic synthesis.

Chemical Structure and Properties

The molecular formula of DBU Formate is C11H16N2O2, and its molecular weight is 212.26 g/mol. The compound exists as a white crystalline solid at room temperature, with a melting point of around 150°C. Its solubility in water is moderate, but it dissolves readily in organic solvents such as ethanol, methanol, and acetone.

One of the most striking features of DBU Formate is its basicity. With a pKa of approximately 19, it is one of the strongest organic bases available. This high basicity makes it an excellent proton acceptor, which is crucial for many catalytic reactions. Additionally, the formate group provides a stabilizing effect, preventing the decomposition of the DBU backbone under harsh conditions.

Product Parameters

To give you a clearer picture of DBU Formate, here’s a detailed table of its key parameters:

Parameter Value
Molecular Formula C11H16N2O2
Molecular Weight 212.26 g/mol
Appearance White crystalline solid
Melting Point 150°C
Boiling Point Decomposes before boiling
Solubility in Water Moderate (20 mg/mL)
Solubility in Ethanol Highly soluble
pKa ~19
Density 1.15 g/cm³
Flash Point >100°C
Storage Conditions Dry, cool, and well-ventilated

Safety and Handling

Like any chemical compound, DBU Formate requires careful handling. It is classified as a flammable solid and should be stored in a dry, cool, and well-ventilated area. Direct contact with skin or eyes should be avoided, as it can cause irritation. In case of inhalation, seek fresh air immediately, and in case of ingestion, consult a physician. Always wear appropriate personal protective equipment (PPE) when working with DBU Formate, including gloves, goggles, and a lab coat.

Applications of DBU Formate in Industrial Processes

Now that we’ve covered the basics, let’s explore the various ways DBU Formate can enhance reaction efficiency in industrial processes. From catalysis to polymerization, this compound has a wide range of applications that can save time, reduce costs, and improve product quality.

1. Catalysis: The Power of Proton Acceptors

One of the most significant applications of DBU Formate is in catalysis. As a strong base, it excels at accepting protons, which is essential for many types of reactions. For example, in Michael additions, DBU Formate can deprotonate the nucleophile, making it more reactive and accelerating the reaction. This is particularly useful in the synthesis of complex organic molecules, where speed and selectivity are critical.

Case Study: Michael Addition in Pharmaceutical Synthesis

In a study published in Organic Letters (2018), researchers used DBU Formate as a catalyst in the Michael addition of malonate to ?,?-unsaturated ketones. The results were impressive: the reaction proceeded with high yield (95%) and excellent diastereoselectivity (98:2 dr). Compared to traditional catalysts like potassium hydroxide, DBU Formate not only increased the reaction rate but also improved the purity of the final product. This is a perfect example of how DBU Formate can streamline the production of pharmaceutical intermediates, reducing both time and waste.

2. Polymerization: A Faster Route to Polymers

Polymerization is another area where DBU Formate shines. In anionic polymerization, the strong basicity of DBU Formate can initiate the polymerization of monomers by deprotonating them. This leads to faster and more controlled polymer growth, resulting in polymers with narrower molecular weight distributions.

Case Study: Anionic Polymerization of Styrene

A research team from the University of Tokyo (2019) investigated the use of DBU Formate in the anionic polymerization of styrene. They found that DBU Formate was able to initiate the polymerization at lower temperatures than conventional initiators, such as butyllithium. Moreover, the polymers produced using DBU Formate had a polydispersity index (PDI) of 1.05, indicating a highly uniform molecular weight. This level of control is crucial for producing high-performance polymers, such as those used in electronics and coatings.

3. Esterification: A Gentle Approach

Esterification is a common reaction in the chemical industry, used to produce everything from perfumes to plastics. Traditionally, esterification reactions require strong acids like sulfuric acid or p-toluenesulfonic acid, which can be corrosive and difficult to handle. DBU Formate offers a gentler alternative, acting as a phase-transfer catalyst in esterification reactions. By facilitating the transfer of reactants between phases, DBU Formate can accelerate the reaction without the need for harsh conditions.

Case Study: Esterification of Fatty Acids

In a study published in Green Chemistry (2020), scientists used DBU Formate to catalyze the esterification of fatty acids with methanol. The reaction was carried out at room temperature, and the yield was over 90%. Importantly, the use of DBU Formate eliminated the need for toxic solvents and minimized the formation of byproducts. This environmentally friendly approach to esterification could have significant implications for the production of biodiesel and other renewable fuels.

4. Carbonyl Reduction: A Selective Catalyst

Carbonyl reduction is a key step in the synthesis of alcohols, which are used in a variety of industries, from cosmetics to pharmaceuticals. DBU Formate can act as a selective catalyst in carbonyl reduction reactions, particularly when paired with hydride donors like sodium borohydride. The high basicity of DBU Formate helps to stabilize the intermediate, leading to faster and more selective reductions.

Case Study: Reduction of Ketones to Alcohols

A group of researchers from the University of California, Berkeley (2017) used DBU Formate to catalyze the reduction of ketones to secondary alcohols. They found that the reaction proceeded with high selectivity, even in the presence of other functional groups. For example, the reduction of acetophenone to 1-phenylethanol was achieved with a yield of 98%, while the competing reduction of a nearby ester group was suppressed. This level of selectivity is invaluable in the synthesis of complex molecules, where unwanted side reactions can lead to impurities and reduced yields.

5. Cross-Coupling Reactions: Bridging the Gap

Cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions, are widely used in the synthesis of biaryls and other carbon-carbon bonds. These reactions typically require expensive and sensitive catalysts, such as palladium complexes. However, DBU Formate can act as a ligand in these reactions, enhancing the activity of the metal catalyst and improving the overall efficiency of the process.

Case Study: Suzuki-Miyaura Coupling

In a study published in Journal of the American Chemical Society (2016), researchers used DBU Formate as a ligand in the Suzuki-Miyaura coupling of aryl bromides. They found that the addition of DBU Formate significantly increased the turnover frequency (TOF) of the palladium catalyst, leading to faster and more complete conversions. The use of DBU Formate also allowed the reaction to proceed at lower temperatures, reducing energy consumption and minimizing the formation of side products.

Advantages of Using DBU Formate

So, why choose DBU Formate over other catalysts and reagents? Here are some of the key advantages:

1. High Basicity and Stability

As mentioned earlier, DBU Formate has a pKa of around 19, making it one of the strongest organic bases available. This high basicity allows it to participate in a wide range of reactions, from deprotonation to stabilization of intermediates. Moreover, the formate group provides additional stability, preventing the decomposition of the DBU backbone under harsh conditions. This makes DBU Formate suitable for use in high-temperature and high-pressure environments, where other bases might degrade.

2. Broad Reactivity

DBU Formate is not limited to a single type of reaction. Its versatility allows it to be used in a wide range of processes, from catalysis to polymerization to esterification. This broad reactivity makes it a valuable tool for chemists and engineers who need to optimize multiple steps in a synthetic pathway.

3. Environmentally Friendly

Unlike many traditional catalysts, DBU Formate is relatively benign and can be used in environmentally friendly processes. For example, in esterification reactions, it eliminates the need for toxic solvents and minimizes the formation of byproducts. This is particularly important in industries like pharmaceuticals and food production, where safety and sustainability are paramount.

4. Cost-Effective

While DBU Formate may not be the cheapest reagent on the market, its ability to increase reaction efficiency and reduce waste can lead to significant cost savings in the long run. By speeding up reactions and improving yields, DBU Formate can help manufacturers reduce their overall production costs and improve their bottom line.

Challenges and Limitations

Of course, no compound is perfect, and DBU Formate is no exception. Here are some of the challenges and limitations associated with its use:

1. Solubility Issues

While DBU Formate is soluble in many organic solvents, its solubility in water is moderate at best. This can be a limitation in reactions that require aqueous conditions, such as certain enzymatic processes. In such cases, alternative catalysts or phase-transfer agents may be necessary.

2. Sensitivity to Moisture

Like many organic bases, DBU Formate is sensitive to moisture, which can lead to degradation over time. This means that it must be stored in a dry environment, and care must be taken to avoid exposure to humidity during handling. While this is not a major issue for most industrial processes, it is something to keep in mind when working with small-scale reactions in the lab.

3. Limited Availability

Although DBU Formate is becoming increasingly popular, it is still not as widely available as some other reagents. This can make it more difficult to source, especially for smaller companies or academic labs. However, as its use becomes more widespread, it is likely that availability will improve.

Conclusion

In conclusion, DBU Formate (CAS 51301-55-4) is a powerful and versatile reagent that has the potential to enhance reaction efficiency in a wide range of industrial processes. From catalysis to polymerization to esterification, its high basicity, stability, and broad reactivity make it an invaluable tool for chemists and engineers. While there are some challenges associated with its use, the benefits far outweigh the drawbacks, particularly in terms of cost savings, environmental impact, and product quality.

As the chemical industry continues to evolve, we can expect to see more innovative applications of DBU Formate in the years to come. Whether you’re synthesizing pharmaceuticals, producing polymers, or refining petrochemicals, this remarkable compound is worth considering for your next project. After all, in the world of industrial chemistry, every little bit of efficiency counts—and DBU Formate just might be the key to unlocking it.

References

  • Chen, X., & Zhang, Y. (2018). Efficient Michael Addition of Malonate to ?,?-Unsaturated Ketones Catalyzed by DBU Formate. Organic Letters, 20(12), 3645-3648.
  • Tanaka, H., & Sato, T. (2019). Anionic Polymerization of Styrene Initiated by DBU Formate. Polymer Journal, 51(3), 245-250.
  • Liu, M., & Wang, J. (2020). Green Esterification of Fatty Acids Catalyzed by DBU Formate. Green Chemistry, 22(5), 1456-1462.
  • Kim, S., & Lee, B. (2017). Selective Reduction of Ketones to Alcohols Using DBU Formate as a Catalyst. Journal of Organic Chemistry, 82(10), 5432-5438.
  • Johnson, A., & Smith, R. (2016). Enhanced Suzuki-Miyaura Coupling Using DBU Formate as a Ligand. Journal of the American Chemical Society, 138(22), 7150-7153.

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The Role of DBU Formate (CAS 51301-55-4) in High-Performance Catalysts

3月 27th, 2025 News

The Role of DBU Formate (CAS 51301-55-4) in High-Performance Catalysts

Introduction

In the world of chemistry, catalysts are like the conductors of an orchestra, guiding and enhancing the performance of chemical reactions. Among the myriad of catalysts available, DBU Formate (CAS 51301-55-4) stands out as a particularly versatile and efficient player. This compound, with its unique properties and structure, has found applications in various fields, from organic synthesis to polymerization, and even in environmental remediation. In this article, we will delve into the role of DBU Formate in high-performance catalysts, exploring its properties, applications, and the latest research findings.

What is DBU Formate?

DBU Formate, also known as 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, is a derivative of the well-known base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). It belongs to the class of organic compounds called bicyclic amines and is characterized by its ability to act as a strong base and nucleophile. The addition of the formate group (HCOO-) to the DBU molecule introduces new functionalities, making it a valuable reagent in catalysis.

Structure and Properties

The molecular formula of DBU Formate is C9H16N2·HCOOH, with a molecular weight of approximately 184.23 g/mol. Its structure consists of a bicyclic amine core with a formate group attached, which imparts both basicity and acidity to the molecule. This dual nature makes DBU Formate a powerful tool in catalytic processes, where it can participate in both acid-catalyzed and base-catalyzed reactions.

Property Value
Molecular Formula C9H16N2·HCOOH
Molecular Weight 184.23 g/mol
Melting Point 145-147°C
Boiling Point Decomposes before boiling
Solubility in Water Slightly soluble
pH Basic (pKa ? 11.5)
Appearance White crystalline solid
Stability Stable under normal conditions

Historical Context

The discovery of DBU Formate dates back to the early 1980s, when researchers were exploring the potential of DBU derivatives in catalysis. Initially, DBU was used as a strong base in organic synthesis, but the introduction of the formate group opened up new possibilities for its use in catalytic systems. Over the years, DBU Formate has gained recognition for its unique properties and has been widely studied in both academic and industrial settings.

Mechanism of Action

Base-Catalyzed Reactions

One of the most significant roles of DBU Formate in catalysis is its ability to act as a strong base. In base-catalyzed reactions, DBU Formate can deprotonate substrates, generating reactive intermediates that can undergo further transformations. For example, in the aldol condensation reaction, DBU Formate can deprotonate a carbonyl compound, forming an enolate ion that can attack another carbonyl group, leading to the formation of a ?-hydroxy ketone or aldehyde.

The strength of DBU Formate as a base is comparable to that of other common bases like potassium tert-butoxide (t-BuOK) and sodium hydride (NaH), but it offers several advantages. Unlike these inorganic bases, DBU Formate is a liquid at room temperature, making it easier to handle and dissolve in organic solvents. Additionally, it is less prone to side reactions and does not produce insoluble salts, which can complicate workup procedures.

Acid-Catalyzed Reactions

While DBU Formate is primarily known for its basicity, the presence of the formate group also allows it to function as a weak acid. This dual nature makes it a versatile catalyst for acid-catalyzed reactions, such as ester hydrolysis and Friedel-Crafts alkylation. In these reactions, the formate group can protonate substrates, facilitating the formation of carbocations or other reactive intermediates.

For instance, in the ester hydrolysis reaction, DBU Formate can protonate the carbonyl oxygen of the ester, weakening the C-O bond and making it more susceptible to nucleophilic attack by water. This leads to the cleavage of the ester bond and the formation of a carboxylic acid and an alcohol. The ability of DBU Formate to act as both a base and an acid in the same reaction mixture is a unique feature that sets it apart from other catalysts.

Dual-Function Catalysis

The dual-functionality of DBU Formate—acting as both a base and an acid—makes it particularly useful in reactions where multiple steps are involved. One such example is the tandem Michael/Michael reaction, where DBU Formate can catalyze both the initial Michael addition and the subsequent intramolecular cyclization. In this reaction, the basicity of DBU Formate promotes the nucleophilic attack of a Michael donor on a Michael acceptor, while the acidic nature of the formate group facilitates the protonation of the resulting enolate intermediate, driving the cyclization step.

This dual-function catalysis is not only efficient but also highly selective, as the two functions work in concert to guide the reaction toward the desired product. The ability to perform multiple catalytic steps in a single pot is a significant advantage in synthetic chemistry, as it reduces the number of isolation and purification steps required, saving time and resources.

Applications in Organic Synthesis

Aldol Condensation

The aldol condensation is one of the most fundamental reactions in organic synthesis, used to form carbon-carbon bonds between carbonyl compounds. DBU Formate has proven to be an excellent catalyst for this reaction, offering high yields and excellent selectivity. In a typical aldol condensation, DBU Formate deprotonates a ketone or aldehyde, forming an enolate ion that can attack another carbonyl compound, leading to the formation of a ?-hydroxy ketone or aldehyde.

One of the key advantages of using DBU Formate in aldol condensations is its ability to promote stereoselective reactions. By carefully controlling the reaction conditions, chemists can achieve high levels of diastereoselectivity and enantioselectivity, which is crucial for the synthesis of chiral compounds. For example, in the asymmetric aldol reaction, the use of chiral auxiliaries in combination with DBU Formate has led to the successful synthesis of complex natural products with high optical purity.

Knoevenagel Condensation

The Knoevenagel condensation is another important reaction in organic synthesis, used to form ?,?-unsaturated compounds from aldehydes or ketones and active methylene compounds. DBU Formate is an effective catalyst for this reaction, promoting the condensation of the two reactants through a base-catalyzed mechanism. The formate group in DBU Formate also plays a role in stabilizing the intermediate enolate, leading to faster reaction rates and higher yields.

One of the challenges in Knoevenagel condensations is the potential for side reactions, such as polymerization or over-condensation. However, the use of DBU Formate has been shown to minimize these side reactions, resulting in cleaner and more efficient reactions. This is particularly important in large-scale industrial applications, where yield and purity are critical factors.

Michael Addition

The Michael addition is a powerful reaction for constructing carbon-carbon bonds between a nucleophile and an ?,?-unsaturated compound. DBU Formate is an excellent catalyst for this reaction, promoting the nucleophilic attack of a Michael donor on a Michael acceptor. The basicity of DBU Formate enhances the nucleophilicity of the donor, while the acidic nature of the formate group facilitates the protonation of the resulting enolate intermediate, driving the reaction to completion.

One of the advantages of using DBU Formate in Michael additions is its ability to promote regioselective reactions. By carefully selecting the reactants and reaction conditions, chemists can control the position of the newly formed carbon-carbon bond, leading to the formation of specific isomers. This is particularly useful in the synthesis of complex molecules, where regiocontrol is essential for achieving the desired structure.

Applications in Polymerization

Ring-Opening Polymerization

Ring-opening polymerization (ROP) is a widely used method for synthesizing polymers from cyclic monomers. DBU Formate has emerged as a promising initiator for ROP, particularly for the polymerization of lactones and cyclic esters. The basicity of DBU Formate promotes the ring-opening of the monomer, while the formate group stabilizes the growing polymer chain, leading to controlled and well-defined polymers.

One of the key advantages of using DBU Formate in ROP is its ability to achieve high molecular weights and narrow polydispersity indices (PDI). This is particularly important in applications where the physical properties of the polymer are critical, such as in biomedical devices or coatings. Additionally, the use of DBU Formate allows for the synthesis of block copolymers, where different monomers can be polymerized sequentially to create polymers with tailored properties.

Living Radical Polymerization

Living radical polymerization (LRP) is a technique used to synthesize polymers with precise molecular weights and controlled architectures. DBU Formate has been explored as a catalyst for LRP, particularly in combination with other initiators such as azo compounds or metal complexes. The basicity of DBU Formate can activate the initiator, leading to the formation of stable radicals that can propagate the polymerization.

One of the challenges in LRP is maintaining livingness throughout the polymerization process, which requires careful control of the reaction conditions. However, the use of DBU Formate has been shown to improve the stability of the radicals, leading to higher livingness and better control over the polymerization. This is particularly important in the synthesis of functional polymers, where the ability to control the molecular weight and architecture is crucial for achieving the desired properties.

Environmental Applications

CO? Capture and Conversion

With the increasing concern over climate change, there is a growing need for technologies that can capture and convert CO? into useful products. DBU Formate has been investigated as a catalyst for CO? capture and conversion, particularly in the context of homogeneous catalysis. The basicity of DBU Formate can promote the nucleophilic attack of CO?, leading to the formation of carbonate or bicarbonate intermediates. These intermediates can then be converted into valuable chemicals, such as cyclic carbonates or polycarbonates, through further reactions.

One of the advantages of using DBU Formate in CO? capture and conversion is its ability to operate under mild conditions, reducing the energy requirements and environmental impact of the process. Additionally, the use of DBU Formate allows for the recycling of the catalyst, making it a sustainable and cost-effective option for CO? utilization.

Water Treatment

Water treatment is another area where DBU Formate has shown promise. The acidic nature of the formate group can be used to neutralize alkaline wastewater, while the basicity of DBU Formate can be used to precipitate heavy metals from aqueous solutions. In particular, DBU Formate has been studied for its ability to remove copper and zinc ions from wastewater, which are common contaminants in industrial effluents.

One of the challenges in water treatment is the development of methods that are both effective and environmentally friendly. The use of DBU Formate offers a green alternative to traditional methods, as it is biodegradable and does not produce harmful byproducts. Additionally, the ability to recover and reuse DBU Formate makes it a sustainable option for water treatment applications.

Safety and Handling

While DBU Formate is a valuable reagent in catalysis, it is important to handle it with care. Like many organic compounds, DBU Formate is flammable and should be stored away from heat and open flames. It is also a skin and eye irritant, so appropriate personal protective equipment (PPE) should be worn when handling the compound. Additionally, DBU Formate should be used in well-ventilated areas to avoid inhalation of vapors.

In terms of disposal, DBU Formate should be handled according to local regulations for hazardous waste. It is biodegradable, but care should be taken to ensure that it does not enter waterways or soil, where it could have adverse effects on the environment.

Conclusion

DBU Formate (CAS 51301-55-4) is a versatile and efficient catalyst with a wide range of applications in organic synthesis, polymerization, and environmental remediation. Its unique structure, combining the basicity of DBU with the acidity of the formate group, allows it to function as both a base and an acid in catalytic processes, making it a valuable tool in the chemist’s toolkit. Whether you’re synthesizing complex molecules, creating advanced materials, or developing sustainable technologies, DBU Formate has the potential to enhance your research and contribute to the advancement of science.

References

  1. Breslow, R., & Helferich, W. (1961). J. Am. Chem. Soc., 83(14), 2908-2910.
  2. Corey, E. J., & Cheng, X. M. (1989). The Logic of Chemical Synthesis. Wiley.
  3. Grubbs, R. H. (2004). Organometallics, 23(1), 1-14.
  4. Matyjaszewski, K., & Xia, J. (2001). Chem. Rev., 101(9), 2921-2990.
  5. Yamamoto, Y. (2005). Catalysis by Supported Metal Complexes. Springer.
  6. Zhang, W., & Wang, L. (2018). Green Chemistry, 20(1), 123-135.
  7. Xu, Q., & Li, Z. (2020). ACS Sustainable Chem. Eng., 8(12), 4567-4575.
  8. Smith, A. B., III, & Kim, J. (2019). J. Org. Chem., 84(10), 6543-6552.
  9. Chen, Y., & Yang, X. (2017). Chem. Commun., 53(45), 6078-6081.
  10. Johnson, J. S., & White, P. S. (2016). Angew. Chem. Int. Ed., 55(22), 6543-6547.

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Advantages of Using DBU Formate (CAS 51301-55-4) in Fine Chemical Production

3月 27th, 2025 News

Advantages of Using DBU Formate (CAS 51301-55-4) in Fine Chemical Production

Introduction

In the world of fine chemical production, the choice of catalysts and reagents can make or break a process. One such versatile and powerful compound that has gained significant attention is DBU Formate (CAS 51301-55-4). This organic compound, with its unique properties, has become an indispensable tool in the hands of chemists, particularly in the synthesis of complex molecules. But what exactly is DBU Formate, and why is it so special? In this article, we will explore the advantages of using DBU Formate in fine chemical production, delving into its chemical structure, physical properties, and applications. We’ll also compare it to other common reagents, highlight its benefits, and provide a comprehensive overview of its role in modern chemistry.

What is DBU Formate?

Chemical Structure and Formula

DBU Formate, scientifically known as 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, is a derivative of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a well-known base in organic synthesis. The addition of the formate group (HCOO-) to DBU imparts unique properties that make it particularly useful in various chemical reactions. The molecular formula of DBU Formate is C11H16N2O2, and its molecular weight is 204.26 g/mol.

Physical Properties

Property Value
Appearance White crystalline solid
Melting Point 155-157°C
Boiling Point Decomposes before boiling
Solubility in Water Slightly soluble
Density 1.19 g/cm³
pKa ~18.5 (in DMSO)

Safety and Handling

DBU Formate is a strong base and should be handled with care. It can cause skin and eye irritation, and inhalation of its vapors may lead to respiratory issues. Therefore, it is essential to work with this compound in a well-ventilated area and use appropriate personal protective equipment (PPE), such as gloves, goggles, and a lab coat. Additionally, it is important to store DBU Formate in a cool, dry place away from moisture and heat sources.

Applications of DBU Formate in Fine Chemical Production

1. As a Catalyst for Carbonyl Condensation Reactions

One of the most significant advantages of DBU Formate is its ability to catalyze carbonyl condensation reactions, such as the Knoevenagel condensation and the Perkin reaction. These reactions are crucial in the synthesis of ?,?-unsaturated compounds, which are building blocks for many pharmaceuticals, agrochemicals, and specialty chemicals.

Knoevenagel Condensation

The Knoevenagel condensation involves the reaction between an aldehyde or ketone and an active methylene compound in the presence of a base catalyst. DBU Formate, with its high basicity and low nucleophilicity, is an excellent choice for this reaction. Unlike other bases, such as sodium hydroxide or potassium hydroxide, DBU Formate does not interfere with the active methylene group, leading to higher yields and fewer side products.

Perkin Reaction

The Perkin reaction is another classic example where DBU Formate shines. In this reaction, an aromatic aldehyde reacts with an acid anhydride in the presence of a base to form a cinnamic acid derivative. DBU Formate’s ability to deprotonate the carboxylic acid group without over-activating the aldehyde makes it an ideal catalyst for this reaction. Moreover, its lower reactivity compared to traditional bases like sodium acetate reduces the risk of unwanted side reactions, such as decarboxylation or polymerization.

2. As a Base for Dehydrohalogenation Reactions

Dehydrohalogenation reactions are essential in the synthesis of alkenes from haloalkanes. DBU Formate, with its strong basicity, can effectively abstract a proton from the ?-carbon of a haloalkane, leading to the formation of a stable alkene. This reaction is particularly useful in the preparation of conjugated dienes, which are important intermediates in the synthesis of natural products and polymers.

Example: Synthesis of Styrene

In the synthesis of styrene from chlorobenzene and acetylene, DBU Formate can be used as a base to facilitate the elimination of hydrogen chloride. The reaction proceeds via a mechanism involving the formation of a benzyne intermediate, which then reacts with acetylene to form styrene. DBU Formate’s high basicity ensures that the reaction occurs efficiently, even at relatively low temperatures, reducing the need for harsh conditions that could lead to unwanted side products.

3. As a Promoter in Asymmetric Catalysis

Asymmetric catalysis is a powerful tool in the synthesis of chiral compounds, which are critical in the pharmaceutical industry. DBU Formate can be used as a promoter in conjunction with chiral catalysts to enhance enantioselectivity. For example, in the asymmetric Michael addition of malonates to ?,?-unsaturated ketones, DBU Formate can help stabilize the transition state, leading to higher enantiomeric excess (ee) values.

Example: Asymmetric Michael Addition

In a study by Smith et al. (2018), DBU Formate was used in combination with a chiral thiourea catalyst to promote the asymmetric Michael addition of malonates to cyclohexenone. The reaction yielded the desired product with an ee value of 95%, significantly higher than when using other bases like triethylamine. The authors attributed this enhanced enantioselectivity to the ability of DBU Formate to form a stable ion pair with the chiral catalyst, thereby stabilizing the transition state and favoring one enantiomer over the other.

4. As a Reagent in Nucleophilic Substitution Reactions

DBU Formate can also serve as a nucleophilic reagent in substitution reactions, particularly in the synthesis of nitrogen-containing compounds. For example, it can be used to introduce a formate group into organic molecules via nucleophilic substitution at electrophilic centers such as halides or sulfonates.

Example: Synthesis of Amines

In a study by Johnson and Lee (2019), DBU Formate was used to synthesize substituted amines from nitriles. The reaction involved the nucleophilic attack of DBU Formate on the carbon-nitrogen triple bond, followed by hydrolysis to yield the corresponding amine. The authors found that DBU Formate was more effective than other nucleophiles, such as hydrazine or ammonia, due to its higher reactivity and selectivity. The reaction proceeded under mild conditions, making it a practical method for the large-scale synthesis of amines.

5. As a Protecting Group for Carboxylic Acids

Carboxylic acids are often protected during synthetic sequences to prevent unwanted side reactions. DBU Formate can be used to convert carboxylic acids into their corresponding esters, which can be easily cleaved later in the synthesis. This protection strategy is particularly useful in multistep syntheses where the carboxylic acid functionality needs to be temporarily masked.

Example: Protection of Carboxylic Acids

In a study by Wang et al. (2020), DBU Formate was used to protect carboxylic acids in the synthesis of a complex natural product. The carboxylic acid was converted into its formate ester using DBU Formate as the reagent. The ester was stable under the reaction conditions and could be easily hydrolyzed back to the carboxylic acid at the end of the synthesis. The authors noted that this protection strategy was more efficient and selective than using other protecting groups, such as tert-butyl esters or benzyl esters.

Comparison with Other Reagents

While DBU Formate is a highly effective reagent in fine chemical production, it is important to compare it with other commonly used reagents to fully appreciate its advantages.

1. DBU vs. DBU Formate

DBU itself is a strong base and is widely used in organic synthesis. However, DBU Formate offers several advantages over DBU:

  • Lower Reactivity: DBU Formate is less reactive than DBU, making it less likely to cause unwanted side reactions. This is particularly important in reactions where the substrate is sensitive to strong bases.
  • Better Solubility: DBU Formate is more soluble in polar solvents, such as water and alcohols, than DBU, which is primarily soluble in non-polar solvents. This makes DBU Formate more versatile in terms of solvent choice.
  • Easier Handling: DBU Formate is a solid at room temperature, whereas DBU is a viscous liquid. This makes DBU Formate easier to handle and measure accurately in the laboratory.

2. Sodium Hydroxide vs. DBU Formate

Sodium hydroxide (NaOH) is a common base used in organic synthesis, but it has several limitations:

  • Corrosiveness: NaOH is highly corrosive and can damage glassware and other laboratory equipment. It also poses a significant safety hazard to researchers.
  • Non-Specificity: NaOH is a non-specific base, meaning it can deprotonate multiple sites on a molecule, leading to unwanted side reactions. DBU Formate, on the other hand, is more selective and can target specific functional groups.
  • Hydrophilicity: NaOH is highly hydrophilic, which can lead to problems in reactions that require anhydrous conditions. DBU Formate, being less hydrophilic, is better suited for these types of reactions.

3. Triethylamine vs. DBU Formate

Triethylamine (TEA) is another common base used in organic synthesis, but it has some drawbacks:

  • Volatility: TEA is volatile and can evaporate during the reaction, leading to inconsistent results. DBU Formate, being a solid, does not suffer from this issue.
  • Odor: TEA has a strong, unpleasant odor that can be irritating to researchers. DBU Formate, while not odorless, has a much milder smell.
  • Reactivity: TEA is less basic than DBU Formate, which can limit its effectiveness in certain reactions. For example, in the Knoevenagel condensation, TEA may not provide the same level of yield and selectivity as DBU Formate.

Conclusion

In conclusion, DBU Formate (CAS 51301-55-4) is a versatile and powerful reagent that offers numerous advantages in fine chemical production. Its unique combination of high basicity, low nucleophilicity, and good solubility makes it an excellent choice for a wide range of reactions, including carbonyl condensations, dehydrohalogenations, asymmetric catalysis, nucleophilic substitutions, and protecting group strategies. Compared to other common reagents, DBU Formate provides superior performance, safety, and ease of handling, making it a valuable tool in the chemist’s arsenal.

As the demand for complex and high-value chemicals continues to grow, the use of DBU Formate in fine chemical production is likely to increase. Whether you’re working on the synthesis of pharmaceuticals, agrochemicals, or specialty materials, DBU Formate is a reagent that deserves serious consideration. So, the next time you’re faced with a challenging synthetic problem, don’t forget to give DBU Formate a try—it might just be the solution you’ve been looking for!

References

  • Smith, J., & Brown, L. (2018). Asymmetric Michael Addition of Malonates to ?,?-Unsaturated Ketones Using DBU Formate as a Promoter. Journal of Organic Chemistry, 83(12), 6789-6795.
  • Johnson, R., & Lee, M. (2019). Synthesis of Amines from Nitriles Using DBU Formate as a Nucleophile. Tetrahedron Letters, 60(45), 5678-5682.
  • Wang, X., Zhang, Y., & Chen, H. (2020). Protection of Carboxylic Acids Using DBU Formate in the Synthesis of Complex Natural Products. Organic Process Research & Development, 24(5), 1234-1240.
  • Patel, A., & Kumar, V. (2017). DBU Formate as a Catalyst for Knoevenagel Condensation: A Comparative Study with Traditional Bases. Synthesis, 49(10), 2345-2352.
  • Li, Z., & Liu, W. (2016). Dehydrohalogenation Reactions Using DBU Formate: Mechanistic Insights and Practical Applications. Chemical Communications, 52(45), 7654-7657.

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