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Optimizing Thermal Stability with DBU Formate (CAS 51301-55-4)

3月 27th, 2025 News

Optimizing Thermal Stability with DBU Formate (CAS 51301-55-4)

Introduction

In the world of chemistry, stability is a key factor in determining the effectiveness and longevity of compounds. Imagine a compound that can withstand the heat of a summer day in Arizona or the frigid cold of a Siberian winter. That’s where DBU Formate (CAS 51301-55-4) comes into play. This versatile chemical not only offers impressive thermal stability but also brings a host of other benefits to various applications. In this article, we will delve into the fascinating world of DBU Formate, exploring its properties, applications, and how it can be optimized for enhanced thermal stability.

What is DBU Formate?

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). It is a white crystalline solid with a melting point of 162-164°C and a molecular weight of 196.23 g/mol. The compound is highly soluble in organic solvents such as ethanol, methanol, and acetone, making it easy to handle in laboratory settings. Its unique structure and properties make it an excellent choice for a wide range of applications, from catalysis to material science.

Why is Thermal Stability Important?

Thermal stability is crucial in many industries, especially those involving high-temperature processes. Think of a car engine running at high speeds or a polymer being molded under extreme heat. If the materials used in these processes are not thermally stable, they can degrade, leading to reduced performance, increased maintenance costs, and even safety hazards. DBU Formate, with its exceptional thermal stability, can help mitigate these issues, ensuring that products remain reliable and efficient over time.

Chemical Structure and Properties

To understand why DBU Formate is so effective, let’s take a closer look at its chemical structure and properties. The compound consists of a bicyclic ring system with two nitrogen atoms, which gives it its characteristic basicity. The formate group (-OCHO) attached to the nitrogen atom adds to its reactivity and solubility in polar solvents.

Molecular Formula and Structure

The molecular formula of DBU Formate is C11H17N2O2. The structure can be visualized as follows:

      N
     / 
    C   C
   /  / 
  C   C   C
 /  /  / 
C   C   C   O
  /  /  /
  C   C   C
    /  /
    C   O
      /
      C
       
        H

This structure provides DBU Formate with several advantages, including:

  • High Basicity: The presence of two nitrogen atoms makes DBU Formate a strong base, which is useful in acid-base reactions.
  • Solubility: The formate group increases the compound’s solubility in polar solvents, making it easier to dissolve and use in various applications.
  • Reactivity: The combination of the bicyclic ring and the formate group allows DBU Formate to participate in a wide range of chemical reactions, including nucleophilic substitution and addition reactions.

Physical and Chemical Properties

Property Value
Molecular Weight 196.23 g/mol
Melting Point 162-164°C
Boiling Point Decomposes before boiling
Density 1.18 g/cm³
Solubility in Water Slightly soluble
Solubility in Ethanol Highly soluble
pH Basic (pKa ? 10.6)
Flash Point >100°C
Autoignition Temperature >200°C

Safety and Handling

While DBU Formate is generally safe to handle, it is important to follow proper safety protocols. The compound is a strong base and can cause skin and eye irritation if mishandled. It is also flammable, so it should be stored in a cool, dry place away from open flames and incompatible materials. Always wear appropriate personal protective equipment (PPE), such as gloves, goggles, and a lab coat, when working with DBU Formate.

Applications of DBU Formate

DBU Formate’s unique properties make it suitable for a wide range of applications across various industries. Let’s explore some of the most common uses of this versatile compound.

1. Catalysis

One of the most significant applications of DBU Formate is in catalysis. As a strong base, it can act as a catalyst in a variety of reactions, including:

  • Esterification: DBU Formate can catalyze the formation of esters from carboxylic acids and alcohols. This reaction is widely used in the production of flavorings, fragrances, and pharmaceuticals.
  • Aldol Condensation: In this reaction, DBU Formate helps form carbon-carbon bonds between aldehydes and ketones, which is essential in the synthesis of complex organic molecules.
  • Michael Addition: DBU Formate can facilitate the addition of nucleophiles to ?,?-unsaturated carbonyl compounds, a reaction commonly used in the preparation of polymers and resins.

2. Polymer Science

DBU Formate plays a crucial role in polymer science, particularly in the development of thermally stable polymers. Polymers are long chains of repeating units that are used in everything from plastics to textiles. However, many polymers are prone to degradation when exposed to high temperatures. By incorporating DBU Formate into the polymer matrix, researchers can improve the thermal stability of the material, allowing it to withstand higher temperatures without losing its structural integrity.

For example, in the production of epoxy resins, DBU Formate can be used as a curing agent. Epoxy resins are widely used in adhesives, coatings, and composites due to their excellent mechanical properties. However, traditional curing agents can limit the thermal stability of the resin. By using DBU Formate, manufacturers can produce epoxy resins that can withstand temperatures up to 200°C, making them ideal for use in aerospace and automotive applications.

3. Pharmaceutical Industry

In the pharmaceutical industry, DBU Formate is used as an intermediate in the synthesis of various drugs. Its ability to participate in nucleophilic substitution reactions makes it a valuable tool in the development of new medications. For instance, DBU Formate can be used to introduce functional groups into drug molecules, enhancing their potency and selectivity.

Additionally, DBU Formate’s thermal stability is particularly useful in the production of heat-sensitive drugs. Many pharmaceuticals are sensitive to temperature changes, which can affect their efficacy and shelf life. By incorporating DBU Formate into the formulation, manufacturers can ensure that the drug remains stable during storage and transportation, even in extreme conditions.

4. Electronics

The electronics industry is another area where DBU Formate shines. In the production of printed circuit boards (PCBs), DBU Formate can be used as a photoresist developer. Photoresists are light-sensitive materials that are used to create patterns on PCBs. After exposure to ultraviolet (UV) light, the photoresist is developed using a solvent, which removes the unexposed areas. DBU Formate, with its high solubility in polar solvents, is an excellent choice for this process, as it can effectively remove the unexposed photoresist without damaging the underlying circuitry.

Moreover, DBU Formate’s thermal stability is crucial in the fabrication of semiconductor devices. During the manufacturing process, semiconductors are subjected to high temperatures, which can cause damage to the delicate structures. By using DBU Formate as a protective coating, engineers can shield the semiconductor from thermal stress, ensuring that it functions properly over time.

5. Environmental Applications

DBU Formate also has potential applications in environmental science. For example, it can be used in the development of advanced materials for carbon capture and storage (CCS). CCS is a technology that captures carbon dioxide (CO?) emissions from industrial processes and stores them underground, reducing the amount of greenhouse gases released into the atmosphere. DBU Formate’s ability to form stable complexes with CO? makes it a promising candidate for this application.

Additionally, DBU Formate can be used in the treatment of wastewater. Many industrial processes generate large amounts of wastewater that contain harmful pollutants. By adding DBU Formate to the wastewater, researchers can neutralize acidic compounds and precipitate heavy metals, making the water safer for disposal or reuse.

Optimizing Thermal Stability

Now that we’ve explored the various applications of DBU Formate, let’s focus on how to optimize its thermal stability. While DBU Formate is already known for its impressive thermal properties, there are several strategies that can further enhance its performance.

1. Encapsulation

One way to improve the thermal stability of DBU Formate is through encapsulation. Encapsulation involves enclosing the compound within a protective shell, which can shield it from external factors such as heat, moisture, and oxygen. There are several methods of encapsulation, including:

  • Polymer Coating: By coating DBU Formate with a thermally stable polymer, such as polyethylene or polystyrene, you can create a barrier that prevents the compound from degrading at high temperatures.
  • Microencapsulation: This technique involves encapsulating DBU Formate within microcapsules, which can be made from materials such as silica or cellulose. Microencapsulation not only improves thermal stability but also enhances the controlled release of the compound, making it ideal for applications such as drug delivery.
  • Nanoencapsulation: Nanoencapsulation involves encapsulating DBU Formate within nanoparticles, which can provide even greater protection against thermal degradation. Nanoparticles have a high surface area-to-volume ratio, which allows for better dispersion and improved performance.

2. Additives

Another strategy for optimizing thermal stability is the use of additives. Additives are substances that are added to a material to enhance its properties. In the case of DBU Formate, certain additives can help improve its thermal resistance. Some common additives include:

  • Antioxidants: Antioxidants, such as vitamin E or butylated hydroxytoluene (BHT), can prevent the oxidation of DBU Formate, which can lead to thermal degradation. By adding antioxidants to the compound, you can extend its shelf life and improve its performance at high temperatures.
  • Heat Stabilizers: Heat stabilizers, such as calcium stearate or zinc oxide, can absorb heat and prevent the breakdown of DBU Formate. These additives are particularly useful in applications where the compound is exposed to prolonged periods of high temperature.
  • Crosslinking Agents: Crosslinking agents, such as divinylbenzene or hexamethoxymethylmelamine (HMMM), can form covalent bonds between DBU Formate molecules, creating a more robust and thermally stable structure. Crosslinking is especially beneficial in the production of polymers and resins.

3. Copolymerization

Copolymerization is a technique that involves combining DBU Formate with other monomers to create a copolymer. A copolymer is a polymer that consists of two or more different types of repeating units. By copolymerizing DBU Formate with other monomers, you can tailor the properties of the resulting material to meet specific requirements. For example, you can create a copolymer that has improved thermal stability, mechanical strength, or chemical resistance.

Some common monomers that can be copolymerized with DBU Formate include:

  • Styrene: Styrene is a versatile monomer that can be used to create copolymers with excellent thermal stability and mechanical strength. Styrene-DBU Formate copolymers are commonly used in the production of plastics and resins.
  • Acrylonitrile: Acrylonitrile is a monomer that imparts excellent chemical resistance and thermal stability to copolymers. Acrylonitrile-DBU Formate copolymers are often used in the production of fibers and films.
  • Butadiene: Butadiene is a monomer that can be used to create copolymers with improved flexibility and impact resistance. Butadiene-DBU Formate copolymers are commonly used in the production of rubber and elastomers.

4. Surface Modification

Surface modification is another approach to optimizing the thermal stability of DBU Formate. By modifying the surface of the compound, you can improve its interaction with other materials and enhance its overall performance. Some common surface modification techniques include:

  • Silanization: Silanization involves treating the surface of DBU Formate with silane coupling agents, which can improve its adhesion to other materials. Silanized DBU Formate is often used in the production of coatings and adhesives.
  • Plasma Treatment: Plasma treatment involves exposing DBU Formate to a plasma, which can modify its surface chemistry and improve its thermal stability. Plasma-treated DBU Formate is commonly used in the production of electronic components and medical devices.
  • Chemical Grafting: Chemical grafting involves attaching functional groups to the surface of DBU Formate, which can improve its compatibility with other materials. Grafted DBU Formate is often used in the production of composite materials and biomaterials.

Conclusion

In conclusion, DBU Formate (CAS 51301-55-4) is a remarkable compound with a wide range of applications, from catalysis to polymer science, pharmaceuticals, electronics, and environmental science. Its unique chemical structure and properties, including high basicity, solubility, and reactivity, make it an invaluable tool in various industries. Moreover, its exceptional thermal stability ensures that it can perform reliably even under extreme conditions.

By employing strategies such as encapsulation, the use of additives, copolymerization, and surface modification, researchers and manufacturers can further optimize the thermal stability of DBU Formate, unlocking new possibilities for innovation and advancement. Whether you’re developing a new drug, creating a cutting-edge electronic device, or working on a sustainable solution for carbon capture, DBU Formate is a powerful ally in your quest for success.

So, the next time you find yourself facing a challenge that requires thermal stability, remember the humble yet mighty DBU Formate. With its versatility and reliability, it just might be the key to solving your problem.

References

  • Smith, J., & Brown, L. (2018). Advanced Catalysis: Principles and Applications. Academic Press.
  • Johnson, R., & Williams, T. (2020). Polymer Science and Engineering. Wiley.
  • Chen, X., & Zhang, Y. (2019). Thermal Stability of Organic Compounds. Elsevier.
  • Lee, K., & Kim, S. (2021). Encapsulation Techniques for Functional Materials. Springer.
  • Patel, M., & Desai, A. (2022). Additives for Enhanced Material Performance. CRC Press.
  • Wang, H., & Liu, Z. (2023). Copolymerization: Theory and Practice. Taylor & Francis.
  • Davis, B., & Thompson, C. (2020). Surface Modification of Polymers. Oxford University Press.
  • Zhao, Q., & Li, J. (2021). Environmental Applications of Advanced Materials. Cambridge University Press.
  • Garcia, F., & Martinez, P. (2019). Pharmaceutical Synthesis Using DBU Derivatives. John Wiley & Sons.
  • Kim, J., & Park, H. (2022). Electronics Materials and Processes. McGraw-Hill Education.

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DBU Phenolate (CAS 57671-19-9) for Long-Term Stability in Chemical Applications

3月 27th, 2025 News

DBU Phenolate (CAS 57671-19-9): A Comprehensive Guide to Long-Term Stability in Chemical Applications

Introduction

In the vast and intricate world of chemistry, stability is a paramount concern. Just as a well-built house stands the test of time, a stable chemical compound ensures reliable performance and longevity in various applications. One such compound that has garnered significant attention for its long-term stability is DBU Phenolate (CAS 57671-19-9). This versatile molecule, derived from the reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with phenol, has found its way into numerous industries, from pharmaceuticals to materials science.

This article delves into the fascinating world of DBU Phenolate, exploring its chemical structure, properties, and applications. We will also discuss the factors that contribute to its long-term stability, making it an invaluable asset in the chemical industry. So, let’s embark on this journey to uncover the secrets of DBU Phenolate and understand why it is a cornerstone in modern chemistry.

Chemical Structure and Properties

Molecular Formula and Structure

DBU Phenolate, also known as 1,8-Diazabicyclo[5.4.0]undec-7-en-7-yl phenoxide, has the molecular formula C13H12N2O. Its structure is a combination of the highly basic DBU moiety and the phenolic oxygen, which imparts both nucleophilic and acidic characteristics to the molecule. The presence of the nitrogen atoms in the DBU ring system makes it a strong base, while the phenolic group provides additional reactivity and stability.

The molecular structure of DBU Phenolate can be visualized as follows:

       N
      / 
     C   C
    /     
   C       C
  /         
C           C
          /
  C       C
        /
    C   C
      /
      O

This unique structure allows DBU Phenolate to participate in a wide range of chemical reactions, making it a valuable catalyst and reagent in organic synthesis.

Physical and Chemical Properties

Property Value
Molecular Weight 216.25 g/mol
Melting Point 120-122°C
Boiling Point Decomposes before boiling
Density 1.15 g/cm³ (at 25°C)
Solubility in Water Slightly soluble
Solubility in Organic Solvents Highly soluble in ethanol, acetone, DMSO
pKa 10.5 (phenolic OH)
pKb -0.5 (DBU moiety)
Appearance White crystalline solid

Reactivity and Stability

DBU Phenolate is a highly reactive compound, thanks to its dual nature as a strong base and a weak acid. The DBU moiety is one of the strongest organic bases known, with a pKb of -0.5, which means it can deprotonate even weak acids like water and alcohols. On the other hand, the phenolic group has a pKa of 10.5, making it a relatively weak acid compared to typical carboxylic acids.

The combination of these two functionalities gives DBU Phenolate a unique set of reactivity profiles. It can act as a base, nucleophile, or even a weak acid, depending on the reaction conditions. This versatility makes it an excellent choice for catalyzing a variety of reactions, including:

  • Aldol Condensation: DBU Phenolate can catalyze the aldol condensation of aldehydes and ketones, leading to the formation of ?-hydroxy carbonyl compounds.
  • Michael Addition: It can promote the Michael addition of nucleophiles to ?,?-unsaturated carbonyl compounds.
  • Esterification: The phenolic group can react with carboxylic acids to form esters, which are important intermediates in many synthetic pathways.
  • Polymerization: DBU Phenolate can initiate the polymerization of certain monomers, such as epoxides and vinyl ethers, due to its ability to abstract protons and generate reactive species.

Despite its high reactivity, DBU Phenolate exhibits remarkable stability under a wide range of conditions. This stability is crucial for its long-term use in industrial processes, where it must withstand exposure to air, moisture, and temperature fluctuations.

Factors Influencing Long-Term Stability

1. Temperature

Temperature is one of the most critical factors affecting the stability of any chemical compound. For DBU Phenolate, moderate temperatures (below 100°C) generally do not pose a significant threat to its stability. However, at higher temperatures, thermal decomposition may occur, leading to the breakdown of the DBU ring system and the loss of its catalytic activity.

To illustrate this point, consider the following data from a study by Smith et al. (2015), which examined the thermal stability of DBU Phenolate in various solvents:

Solvent Temperature (°C) Decomposition (%)
Ethanol 80 5
Acetone 90 10
DMSO 100 15
Toluene 120 25

As you can see, the decomposition rate increases with both temperature and solvent polarity. Therefore, it is essential to store DBU Phenolate at room temperature and avoid prolonged exposure to heat sources.

2. Moisture

Moisture can have a profound impact on the stability of DBU Phenolate, particularly when it comes to its basicity. The presence of water can lead to the hydrolysis of the DBU ring, resulting in the formation of less active byproducts. Additionally, moisture can promote the oxidation of the phenolic group, further compromising the compound’s stability.

To mitigate the effects of moisture, it is recommended to store DBU Phenolate in a dry environment, preferably under an inert atmosphere such as nitrogen or argon. Desiccants, such as silica gel, can also be used to absorb any residual moisture in the storage container.

3. Light

While DBU Phenolate is generally stable to light, prolonged exposure to UV radiation can cause photochemical degradation. This is especially true for solutions of DBU Phenolate in transparent solvents, where the light can penetrate deep into the solution and initiate radical reactions.

To prevent light-induced degradation, it is advisable to store DBU Phenolate in amber-colored bottles or in containers wrapped in aluminum foil. If the compound is to be used in a photoreactive process, appropriate UV filters should be employed to protect it from harmful radiation.

4. Oxidizing Agents

DBU Phenolate is susceptible to oxidation, particularly in the presence of strong oxidizing agents such as hydrogen peroxide, ozone, or nitric acid. Oxidation can lead to the formation of quinone derivatives, which are much less reactive and may interfere with the desired chemical reactions.

To avoid oxidation, it is important to handle DBU Phenolate with care, avoiding contact with oxidizing agents and using reducing agents if necessary. In some cases, antioxidants such as butylated hydroxytoluene (BHT) can be added to the reaction mixture to protect the compound from oxidative degradation.

5. Metal Ions

Certain metal ions, particularly transition metals like iron, copper, and manganese, can catalyze the decomposition of DBU Phenolate. These metals can form complexes with the phenolic oxygen, leading to the cleavage of the DBU ring and the loss of catalytic activity.

To prevent metal-catalyzed decomposition, it is recommended to use metal-free solvents and reagents whenever possible. If metal contamination is unavoidable, chelating agents such as EDTA or citric acid can be added to sequester the metal ions and inhibit their catalytic activity.

Applications of DBU Phenolate

1. Pharmaceutical Industry

DBU Phenolate has found extensive use in the pharmaceutical industry, particularly in the synthesis of active pharmaceutical ingredients (APIs). Its ability to catalyze key reactions, such as aldol condensation and Michael addition, makes it an indispensable tool for drug discovery and development.

One notable example is the synthesis of statins, a class of drugs used to lower cholesterol levels. DBU Phenolate can catalyze the aldol condensation of acetoacetic ester with benzaldehyde, leading to the formation of the core structure of statins. This reaction is highly efficient and selective, producing high yields of the desired product with minimal side reactions.

2. Materials Science

In the field of materials science, DBU Phenolate is used as a catalyst for the polymerization of various monomers, including epoxides and vinyl ethers. The resulting polymers have a wide range of applications, from adhesives and coatings to electronic materials and biomedical devices.

For instance, DBU Phenolate can initiate the ring-opening polymerization of cyclohexene oxide, leading to the formation of poly(cyclohexene oxide), a high-performance polymer with excellent thermal stability and mechanical properties. This polymer is used in the production of advanced composites, which are lightweight and durable, making them ideal for aerospace and automotive applications.

3. Organic Synthesis

DBU Phenolate is a versatile reagent in organic synthesis, capable of promoting a wide variety of reactions. Its strong basicity and nucleophilicity make it an excellent catalyst for reactions involving carbonyl compounds, such as aldol condensation, Michael addition, and Mannich reactions.

In addition to its catalytic properties, DBU Phenolate can also serve as a protecting group for alcohols and phenols. By reacting with these functional groups, DBU Phenolate forms stable ethers that can be easily cleaved under mild conditions, allowing for the selective protection and deprotection of sensitive functionalities.

4. Analytical Chemistry

DBU Phenolate has also found applications in analytical chemistry, particularly in the determination of trace amounts of metals and other analytes. Its ability to form stable complexes with metal ions makes it a useful reagent for spectrophotometric and chromatographic analysis.

For example, DBU Phenolate can be used to complex with copper(II) ions, forming a colored complex that can be detected at low concentrations. This method has been used to monitor copper contamination in environmental samples, providing a simple and cost-effective alternative to more sophisticated techniques.

Conclusion

In conclusion, DBU Phenolate (CAS 57671-19-9) is a remarkable compound that combines the strengths of a strong base and a weak acid, making it a valuable tool in a wide range of chemical applications. Its long-term stability, influenced by factors such as temperature, moisture, light, oxidizing agents, and metal ions, ensures that it remains a reliable and efficient reagent in both laboratory and industrial settings.

From its role in the synthesis of life-saving drugs to its use in the development of advanced materials, DBU Phenolate continues to play a pivotal role in modern chemistry. As research in this field progresses, we can expect to see even more innovative applications of this versatile compound, further expanding its utility and impact.

So, the next time you encounter DBU Phenolate in your work, remember that it is not just another chemical compound—it is a key player in the ongoing quest to push the boundaries of what is possible in chemistry. And who knows? Maybe one day, you’ll discover a new application for this fascinating molecule that will change the world.

References:

  1. Smith, J., Brown, L., & Johnson, M. (2015). Thermal Stability of DBU Phenolate in Various Solvents. Journal of Organic Chemistry, 80(12), 6543-6550.
  2. Zhang, Y., & Wang, X. (2018). Catalytic Applications of DBU Phenolate in Pharmaceutical Synthesis. Chemical Reviews, 118(15), 7234-7250.
  3. Lee, H., & Kim, J. (2020). Polymerization of Epoxides Using DBU Phenolate as a Catalyst. Macromolecules, 53(10), 4215-4222.
  4. Patel, R., & Kumar, V. (2019). Analytical Applications of DBU Phenolate in Metal Ion Detection. Analytical Chemistry, 91(18), 11542-11548.
  5. Chen, S., & Li, W. (2017). Protecting Group Chemistry Using DBU Phenolate. Tetrahedron Letters, 58(45), 4955-4958.

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Applications of DBU Formate (CAS 51301-55-4) in Chemical Synthesis

3月 27th, 2025 News

Applications of DBU Formate (CAS 51301-55-4) in Chemical Synthesis

Introduction

DBU formate, with the chemical formula C12H17NO2 and CAS number 51301-55-4, is a versatile reagent that has garnered significant attention in the field of chemical synthesis. This compound, derived from 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), combines the strong basicity of DBU with the carboxylate functionality of formic acid. The unique properties of DBU formate make it an invaluable tool in various synthetic transformations, ranging from organic chemistry to materials science.

In this comprehensive article, we will delve into the applications of DBU formate in chemical synthesis, exploring its role in different reactions, its advantages over other reagents, and its potential for future developments. We will also provide detailed product parameters and reference relevant literature to ensure a thorough understanding of this fascinating compound.

Structure and Properties

Before diving into the applications, let’s take a moment to understand the structure and properties of DBU formate. The compound consists of a bicyclic ring system with two nitrogen atoms, which imparts its strong basicity. The formate group (COO-) adds polarity and reactivity, making DBU formate a powerful nucleophile and base.

Property Value
Molecular Formula C12H17NO2
Molecular Weight 215.27 g/mol
CAS Number 51301-55-4
Melting Point 160-162°C
Boiling Point Decomposes before boiling
Solubility in Water Soluble
pKa ~12.5 (basicity)
Appearance White crystalline solid
Odor Characteristic amine odor

The high pKa value of DBU formate indicates its strong basicity, which is crucial for many synthetic reactions. Additionally, its solubility in water and polar organic solvents makes it easy to handle and integrate into various reaction conditions.

Applications in Organic Synthesis

1. Catalysis in Condensation Reactions

One of the most prominent applications of DBU formate is as a catalyst in condensation reactions. These reactions involve the formation of a new carbon-carbon bond between two molecules, often accompanied by the elimination of a small molecule such as water or alcohol. DBU formate’s strong basicity and nucleophilicity make it an excellent catalyst for these types of reactions.

Example: Aldol Condensation

The aldol condensation is a classic example of a condensation reaction where an enolate ion reacts with an aldehyde or ketone to form a ?-hydroxy carbonyl compound. DBU formate can effectively catalyze this reaction by deprotonating the ?-carbon of the carbonyl compound, forming an enolate intermediate. This intermediate then attacks the electrophilic carbonyl carbon of another molecule, leading to the formation of the desired product.

[
text{R-C=O} + text{R’-C=O} xrightarrow{text{DBU formate}} text{R-C(R’)-C(OH)-C=O}
]

Compared to traditional bases like sodium hydroxide or potassium tert-butoxide, DBU formate offers several advantages. Its lower toxicity and higher solubility in organic solvents make it more user-friendly and environmentally friendly. Moreover, DBU formate can be used in milder reaction conditions, reducing the risk of side reactions and improving yield.

Literature Reference:

  • Organic Syntheses (1995) – A study comparing the efficiency of various bases in aldol condensation reactions found that DBU formate provided higher yields and better selectivity compared to other commonly used bases.

2. Ring-Opening Reactions

DBU formate is also highly effective in ring-opening reactions, particularly those involving epoxides and aziridines. The strong basicity of DBU formate facilitates the nucleophilic attack on the strained cyclic compounds, leading to the formation of open-chain products.

Example: Epoxide Ring Opening

Epoxides are three-membered cyclic ethers that are prone to ring-opening reactions due to the high ring strain. DBU formate can act as a nucleophile, attacking the electrophilic carbon of the epoxide and opening the ring. The resulting product is a substituted alcohol or ether, depending on the nature of the reactants.

[
text{R-O-R’} + text{DBU formate} rightarrow text{R-CH(OH)-R’}
]

This reaction is particularly useful in the synthesis of complex organic molecules, where the introduction of a hydroxyl group can serve as a key functional group for further transformations. DBU formate’s ability to selectively open epoxides under mild conditions makes it a valuable tool in the chemist’s arsenal.

Literature Reference:

  • Journal of Organic Chemistry (2002) – A paper describing the use of DBU formate in the selective ring-opening of epoxides reported that the reagent provided excellent regioselectivity and high yields, even in the presence of competing functionalities.

3. Carbon-Nitrogen Bond Formation

Another important application of DBU formate is in the formation of carbon-nitrogen bonds, which are essential in the synthesis of amines, amides, and other nitrogen-containing compounds. DBU formate can act as a nucleophile, attacking electrophilic carbon centers to form new C-N bonds.

Example: Urea Synthesis

Ureas are important compounds in both industrial and pharmaceutical applications. DBU formate can be used to synthesize ureas by reacting with isocyanates or carbamoyl chlorides. The strong basicity of DBU formate deprotonates the amine, making it more nucleophilic and capable of attacking the electrophilic carbon of the isocyanate.

[
text{RN=C=O} + text{NH}_2text{R’} + text{DBU formate} rightarrow text{RNHCONHR’}
]

This method is particularly advantageous because it avoids the use of harsh conditions and toxic reagents, making it more environmentally friendly and safer to handle. Additionally, the high yield and purity of the resulting urea make DBU formate an attractive choice for large-scale production.

Literature Reference:

  • Tetrahedron Letters (2008) – A study on the synthesis of ureas using DBU formate as a catalyst demonstrated that the reagent provided excellent yields and selectivity, even in the presence of sensitive functional groups.

4. Polymerization Reactions

DBU formate has also found applications in polymer chemistry, particularly in the initiation of cationic and anionic polymerizations. The strong basicity of DBU formate allows it to generate active species that can initiate the polymerization of various monomers, leading to the formation of polymers with controlled molecular weights and architectures.

Example: Anionic Polymerization of Styrene

Anionic polymerization is a process where a nucleophilic initiator attacks the electrophilic carbon of a vinyl monomer, leading to the formation of a growing polymer chain. DBU formate can act as an initiator by deprotonating the monomer, generating a carbanion that propagates the polymerization.

[
text{Ph-CH=CH}_2 + text{DBU formate} rightarrow text{Ph-CH(-)}text{CH}_2text{-DBU formate}
]

This method is particularly useful for synthesizing well-defined polymers with narrow molecular weight distributions. DBU formate’s ability to initiate polymerization under mild conditions and its compatibility with a wide range of monomers make it a valuable reagent in polymer chemistry.

Literature Reference:

  • Macromolecules (2010) – A study on the anionic polymerization of styrene using DBU formate as an initiator reported that the reagent provided excellent control over molecular weight and polydispersity, making it suitable for the synthesis of advanced materials.

Advantages of DBU Formate in Chemical Synthesis

1. Mild Reaction Conditions

One of the most significant advantages of DBU formate is its ability to perform reactions under mild conditions. Traditional bases like sodium hydride or potassium tert-butoxide often require high temperatures or strong solvents, which can lead to side reactions or degradation of sensitive substrates. In contrast, DBU formate can operate at room temperature or slightly elevated temperatures, reducing the risk of unwanted byproducts and improving overall yield.

2. High Selectivity

DBU formate’s strong basicity and nucleophilicity allow it to selectively target specific functional groups in a molecule, minimizing the formation of side products. This is particularly important in complex organic synthesis, where multiple reactive sites may be present. By carefully controlling the reaction conditions, chemists can achieve high levels of regioselectivity and stereoselectivity, leading to the formation of pure, desired products.

3. Environmental Friendliness

Compared to many traditional reagents, DBU formate is relatively environmentally friendly. It is less toxic and easier to handle, reducing the risk of exposure to hazardous chemicals. Additionally, DBU formate can be used in aqueous or polar organic solvents, which are generally more eco-friendly than non-polar solvents like dichloromethane or toluene. This makes DBU formate an attractive choice for green chemistry initiatives.

4. Versatility

DBU formate’s versatility is one of its most appealing features. It can be used in a wide range of reactions, from simple condensations to complex polymerizations. Its ability to function as both a base and a nucleophile makes it a "Swiss Army knife" in the chemist’s toolkit, capable of addressing a variety of synthetic challenges.

Future Prospects and Challenges

While DBU formate has already proven its worth in many areas of chemical synthesis, there are still opportunities for further development. One area of interest is the use of DBU formate in asymmetric synthesis, where the goal is to introduce chirality into molecules with high enantioselectivity. Researchers are exploring ways to modify DBU formate or combine it with chiral auxiliaries to achieve this goal.

Another challenge is the scalability of reactions involving DBU formate. While the reagent works well in small-scale laboratory settings, its performance in large-scale industrial processes has yet to be fully optimized. Chemists are working to develop more efficient and cost-effective methods for producing DBU formate and incorporating it into industrial-scale reactions.

Finally, there is ongoing research into the environmental impact of DBU formate. While it is generally considered more environmentally friendly than many traditional reagents, there is still a need to assess its long-term effects on ecosystems and human health. Continued studies in this area will help ensure that DBU formate remains a sustainable and responsible choice for chemical synthesis.

Conclusion

DBU formate (CAS 51301-55-4) is a remarkable reagent that has found widespread applications in chemical synthesis. Its strong basicity, nucleophilicity, and versatility make it an invaluable tool for chemists working in a variety of fields, from organic synthesis to polymer chemistry. As research continues to uncover new uses for this compound, DBU formate is likely to play an increasingly important role in the development of new materials and pharmaceuticals.

By understanding the structure, properties, and applications of DBU formate, chemists can harness its full potential to create innovative solutions to complex synthetic problems. Whether you’re a seasoned researcher or a student just starting out, DBU formate is a reagent worth keeping in your toolbox.

References

  • Organic Syntheses (1995). Comparison of various bases in aldol condensation reactions.
  • Journal of Organic Chemistry (2002). Selective ring-opening of epoxides using DBU formate.
  • Tetrahedron Letters (2008). Synthesis of ureas using DBU formate as a catalyst.
  • Macromolecules (2010). Anionic polymerization of styrene using DBU formate as an initiator.
  • Green Chemistry (2015). Environmental impact of DBU formate in chemical synthesis.
  • Advanced Materials (2018). Asymmetric synthesis using modified DBU formate.

In summary, DBU formate is a powerful and versatile reagent that has revolutionized the field of chemical synthesis. Its unique properties make it an ideal choice for a wide range of reactions, and its environmental friendliness ensures that it will continue to be a popular choice for researchers and industry professionals alike.

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