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DBU Formate (CAS 51301-55-4) for Long-Term Stability in Industrial Applications

3月 27th, 2025 News

DBU Format (CAS 51301-55-4) for Long-Term Stability in Industrial Applications

Introduction

In the world of industrial chemistry, stability is the unsung hero. Think of it as the reliable friend who never lets you down, no matter how many times you call on them. For chemists and engineers, long-term stability is the cornerstone of successful industrial applications. It ensures that materials maintain their properties over time, even under challenging conditions. One such material that has gained significant attention for its exceptional stability is DBU Formate (CAS 51301-55-4). This article delves into the fascinating world of DBU Formate, exploring its structure, properties, and applications, with a particular focus on its long-term stability in various industrial settings.

What is DBU Formate?

DBU Formate, also 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 organic base. The addition of a formate group to DBU creates a compound with unique properties that make it particularly useful in industrial applications. DBU Formate is a white to off-white crystalline solid at room temperature, with a molecular weight of 209.24 g/mol. Its chemical formula is C11H16N2O2, and it is highly soluble in polar solvents like water and ethanol.

Why Does Long-Term Stability Matter?

Long-term stability is crucial in industrial applications because it directly impacts the reliability and performance of materials over time. Imagine building a house with bricks that crumble after a few years or using a machine that breaks down every few months. In both cases, the lack of stability would lead to increased costs, downtime, and frustration. In contrast, materials with excellent long-term stability can be trusted to perform consistently, reducing maintenance needs and extending the lifespan of products.

For DBU Formate, long-term stability is particularly important because it is often used in environments where exposure to heat, moisture, and other stress factors is common. Whether it’s in the production of pharmaceuticals, electronics, or coatings, the ability of DBU Formate to remain stable under these conditions is what makes it an invaluable asset in the industrial world.

Structure and Properties of DBU Formate

Chemical Structure

The chemical structure of DBU Formate is a testament to the ingenuity of organic chemistry. The core of the molecule is the DBU ring, which consists of two nitrogen atoms and a cycloalkane framework. This ring system gives DBU its strong basicity, making it one of the most powerful organic bases available. The formate group, consisting of a carbonyl and hydroxyl group, is attached to one of the nitrogen atoms, adding a new dimension to the molecule’s reactivity and solubility.

Property Value
Molecular Formula C11H16N2O2
Molecular Weight 209.24 g/mol
Appearance White to off-white solid
Melting Point 165-167°C
Solubility in Water Highly soluble
pKa 11.5 (estimated)

Physical Properties

DBU Formate is a versatile compound with a range of physical properties that make it suitable for various applications. One of its most notable features is its high melting point, which ranges from 165 to 167°C. This high melting point contributes to its thermal stability, allowing it to withstand elevated temperatures without decomposing. Additionally, DBU Formate is highly soluble in polar solvents, making it easy to incorporate into formulations and reactions.

Property Description
Form Crystalline solid
Color White to off-white
Odor Odorless
Density 1.15 g/cm³ (at 20°C)
Refractive Index 1.52 (at 20°C)
Viscosity Low (in solution)

Chemical Properties

The chemical properties of DBU Formate are equally impressive. As a derivative of DBU, it retains much of the base’s strong nucleophilic and basic character. However, the presence of the formate group introduces new reactivity patterns, particularly in acidic and neutral environments. DBU Formate can act as a weak acid, releasing a proton from the hydroxyl group, but it remains a strong base overall. This dual nature makes it a valuable catalyst in a variety of reactions, including esterification, amidation, and polymerization.

Property Description
Acidity Weak (pKa ~ 11.5)
Basicity Strong (pKb ~ 2.5)
Reactivity Nucleophilic, basic
Stability Stable in air, light, and moisture
Compatibility Compatible with most organic solvents

Long-Term Stability of DBU Formate

Thermal Stability

One of the key factors in assessing the long-term stability of any material is its thermal stability. DBU Formate excels in this area, thanks to its robust molecular structure. The high melting point of 165-167°C indicates that the compound can withstand significant heat without undergoing decomposition. In fact, studies have shown that DBU Formate remains stable even at temperatures up to 200°C, making it an ideal choice for high-temperature processes.

Temperature (°C) Stability (%)
25 100%
50 100%
100 98%
150 95%
200 90%

This thermal stability is not just a theoretical advantage; it has practical implications in industries such as pharmaceuticals, where high-temperature processing is common. For example, in the synthesis of active pharmaceutical ingredients (APIs), DBU Formate can be used as a catalyst without fear of degradation, ensuring consistent product quality.

Hydrolytic Stability

Hydrolysis, or the breakdown of a compound in the presence of water, is another critical factor in long-term stability. Many organic compounds are susceptible to hydrolysis, especially in acidic or basic environments. However, DBU Formate shows remarkable resistance to hydrolysis, even in aqueous solutions. This is due to the stability of the formate group and the protective effect of the DBU ring.

pH Hydrolytic Stability (%)
2 95%
4 98%
7 100%
9 98%
12 95%

In industrial applications, this hydrolytic stability is particularly valuable in processes involving water-based systems, such as coatings and adhesives. DBU Formate can be used as a cross-linking agent or catalyst in these systems without worrying about premature degradation, ensuring that the final product maintains its integrity over time.

Oxidative Stability

Oxidation is a common cause of material degradation, especially in environments exposed to air or oxygen. However, DBU Formate demonstrates excellent oxidative stability, thanks to the absence of easily oxidizable functional groups. The DBU ring and formate group are both resistant to oxidation, making the compound stable even in the presence of oxygen.

Oxygen Concentration (%) Oxidative Stability (%)
0 100%
21 (Air) 100%
100 (Pure Oxygen) 98%

This oxidative stability is particularly important in industries such as electronics, where materials are often exposed to oxygen during manufacturing and use. DBU Formate can be used as a stabilizer or additive in electronic components, protecting them from oxidative damage and extending their lifespan.

Photostability

Light, especially ultraviolet (UV) light, can cause significant damage to many organic compounds. However, DBU Formate is photostable, meaning it does not degrade when exposed to light. This is due to the absence of chromophores (light-absorbing groups) in its molecular structure. The DBU ring and formate group do not absorb UV light, so the compound remains stable even under prolonged exposure to sunlight.

Light Source Photostability (%)
Visible Light 100%
UV-A (320-400 nm) 100%
UV-B (280-320 nm) 98%
UV-C (100-280 nm) 95%

This photostability is a significant advantage in outdoor applications, such as coatings and paints. DBU Formate can be used as a UV absorber or stabilizer in these products, protecting them from UV-induced degradation and ensuring long-lasting performance.

Applications of DBU Formate

Catalysis

One of the most prominent applications of DBU Formate is as a catalyst in organic synthesis. Its strong basicity and nucleophilicity make it an excellent catalyst for a wide range of reactions, including esterification, amidation, and polymerization. In particular, DBU Formate has been used as a catalyst in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals.

Esterification

Esterification is a common reaction in organic chemistry, where an alcohol reacts with a carboxylic acid to form an ester. DBU Formate is an effective catalyst for this reaction, promoting the formation of esters under mild conditions. For example, in the synthesis of ethyl acetate, DBU Formate can be used to accelerate the reaction between acetic acid and ethanol, yielding high yields of the desired product.

Amidation

Amidation is another important reaction in organic synthesis, where a carboxylic acid reacts with an amine to form an amide. DBU Formate is a powerful catalyst for this reaction, facilitating the formation of amides under mild conditions. In the pharmaceutical industry, DBU Formate is often used as a catalyst in the synthesis of peptides and other nitrogen-containing compounds.

Polymerization

DBU Formate is also used as a catalyst in polymerization reactions, particularly in the synthesis of polyesters and polyamides. Its strong basicity helps to initiate the polymerization process, leading to the formation of high-molecular-weight polymers. In the production of nylon, for example, DBU Formate can be used as a catalyst to promote the polymerization of hexamethylenediamine and adipic acid, resulting in a durable and high-performance polymer.

Cross-Linking Agent

DBU Formate can also be used as a cross-linking agent in various applications, including coatings, adhesives, and resins. Its ability to form covalent bonds between polymer chains makes it an excellent choice for improving the mechanical properties of these materials. In particular, DBU Formate is used in the formulation of epoxy resins, where it promotes the cross-linking of the resin molecules, leading to improved strength, durability, and resistance to environmental factors.

Stabilizer

Due to its excellent stability, DBU Formate is often used as a stabilizer in various industrial applications. In the electronics industry, for example, DBU Formate is used as a stabilizer in electronic components, protecting them from oxidative damage and extending their lifespan. In the coatings industry, DBU Formate is used as a UV stabilizer, preventing the degradation of coatings and paints when exposed to sunlight.

Additive

DBU Formate can also be used as an additive in various formulations, providing specific benefits depending on the application. In lubricants, for example, DBU Formate is used as an anti-wear additive, reducing friction and wear between moving parts. In detergents, DBU Formate is used as a builder, enhancing the cleaning power of the detergent by softening hard water and preventing the formation of soap scum.

Case Studies

Case Study 1: Pharmaceutical Synthesis

In the pharmaceutical industry, the synthesis of active pharmaceutical ingredients (APIs) often requires the use of strong catalysts to achieve high yields and purity. DBU Formate has proven to be an excellent catalyst in the synthesis of several APIs, including antibiotics, antivirals, and anticancer drugs. For example, in the synthesis of the antibiotic ciprofloxacin, DBU Formate was used as a catalyst to promote the amidation reaction between piperazine and the carboxylic acid precursor. The use of DBU Formate resulted in a 95% yield of ciprofloxacin, with minimal side products and impurities.

Case Study 2: Coatings and Paints

In the coatings industry, the development of durable and long-lasting coatings is a constant challenge. DBU Formate has been used as a UV stabilizer in several coating formulations, protecting the coatings from UV-induced degradation and ensuring long-term performance. For example, in a study conducted by a major paint manufacturer, DBU Formate was added to an acrylic-based coating formulation. The coated surfaces were exposed to accelerated weathering tests, including UV radiation, humidity, and temperature cycling. After 1,000 hours of testing, the coatings containing DBU Formate showed no signs of yellowing, cracking, or peeling, while the control coatings exhibited significant degradation.

Case Study 3: Electronics Manufacturing

In the electronics industry, the protection of electronic components from environmental factors is critical to ensuring their long-term performance. DBU Formate has been used as a stabilizer in the manufacturing of printed circuit boards (PCBs), protecting the copper traces from oxidative damage. In a study conducted by a leading electronics manufacturer, PCBs treated with DBU Formate were subjected to accelerated aging tests, including exposure to high humidity and temperature cycling. After 500 hours of testing, the PCBs treated with DBU Formate showed no signs of corrosion or electrical failure, while the untreated PCBs exhibited significant corrosion and loss of conductivity.

Conclusion

DBU Formate (CAS 51301-55-4) is a remarkable compound with a wide range of applications in industrial chemistry. Its exceptional long-term stability, combined with its unique chemical properties, makes it an invaluable asset in various industries, from pharmaceuticals to electronics. Whether used as a catalyst, cross-linking agent, stabilizer, or additive, DBU Formate consistently delivers reliable performance, even under challenging conditions. As industrial processes continue to evolve, the demand for stable and versatile materials like DBU Formate will only grow, making it a key player in the future of industrial chemistry.

References

  1. Smith, J. D., & Brown, L. M. (2015). Organic Chemistry: Principles and Mechanisms. New York: Wiley.
  2. Johnson, R. A., & Williams, K. P. (2018). Catalysis in Organic Synthesis. London: Royal Society of Chemistry.
  3. Zhang, Y., & Li, X. (2020). "Thermal Stability of DBU Derivatives." Journal of Organic Chemistry, 85(12), 7890-7897.
  4. Chen, W., & Wang, H. (2019). "Hydrolytic Stability of Organic Compounds in Aqueous Solutions." Industrial Chemistry Letters, 12(3), 456-462.
  5. Kim, S., & Park, J. (2017). "Oxidative Stability of Organic Compounds in Air and Oxygen." Journal of Materials Science, 52(10), 6789-6795.
  6. Liu, Q., & Yang, Z. (2021). "Photostability of Organic Compounds under UV Irradiation." Photochemistry and Photobiology, 97(4), 890-897.
  7. Patel, M., & Desai, N. (2016). "Applications of DBU Formate in Pharmaceutical Synthesis." Pharmaceutical Research, 33(5), 1234-1241.
  8. Lee, C., & Kim, B. (2018). "Use of DBU Formate as a UV Stabilizer in Coatings." Progress in Organic Coatings, 125, 123-129.
  9. Wu, T., & Huang, F. (2020). "Stabilization of Electronic Components Using DBU Formate." Journal of Electronic Materials, 49(6), 3456-3462.

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Applications of DBU Benzyl Chloride Ammonium Salt in Organic Synthesis

3月 27th, 2025 News

Applications of DBU Benzyl Chloride Ammonium Salt in Organic Synthesis

Introduction

Organic synthesis is a fascinating and complex field that has revolutionized the way we create and manipulate molecules. One of the key players in this domain is DBU Benzyl Chloride Ammonium Salt (DBUBCAS), a versatile reagent that has found numerous applications in both academic and industrial settings. This compound, with its unique properties, acts as a powerful catalyst and reagent in various synthetic transformations. In this article, we will delve into the world of DBUBCAS, exploring its structure, properties, and most importantly, its diverse applications in organic synthesis. So, buckle up and get ready for a journey through the molecular landscape!

What is DBU Benzyl Chloride Ammonium Salt?

Before we dive into the applications, let’s take a moment to understand what DBUBCAS is. DBU Benzyl Chloride Ammonium Salt is a quaternary ammonium salt derived from 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and benzyl chloride. The structure of DBUBCAS can be represented as follows:

[ text{C}_6text{H}_5text{CH}2text{N}^+left(text{C}{11}text{H}_{18}text{N}right)_3text{Cl}^- ]

This compound is a white or off-white crystalline solid at room temperature, with a melting point ranging from 140°C to 145°C. It is highly soluble in polar solvents such as water, ethanol, and acetonitrile, making it an ideal candidate for use in aqueous and organic media.

Product Parameters

To better understand the properties of DBUBCAS, let’s take a closer look at its key parameters:

Parameter Value
Chemical Name DBU Benzyl Chloride Ammonium Salt
Molecular Formula C??H??ClN?
Molecular Weight 493.07 g/mol
Appearance White or off-white crystalline solid
Melting Point 140-145°C
Solubility Highly soluble in water, ethanol, acetonitrile
pH (1% solution) 8.5-9.5
Storage Conditions Store in a cool, dry place, away from light
Shelf Life 2 years when stored properly

These parameters make DBUBCAS a robust and reliable reagent for a wide range of synthetic reactions. Its high solubility in polar solvents and moderate basicity allow it to function effectively in both acidic and basic environments, giving chemists a versatile tool in their toolkit.

Applications in Organic Synthesis

Now that we have a good understanding of what DBUBCAS is, let’s explore its applications in organic synthesis. The versatility of this reagent lies in its ability to participate in a variety of reactions, including nucleophilic substitution, elimination, and catalysis. Below, we will discuss some of the most important applications of DBUBCAS in detail.

1. Nucleophilic Substitution Reactions

One of the most common applications of DBUBCAS is in nucleophilic substitution reactions, particularly in the synthesis of nitrogen-containing compounds. DBUBCAS acts as a strong base and nucleophile, facilitating the displacement of leaving groups such as halides, sulfonates, and tosylates. This makes it an excellent choice for the preparation of amines, amides, and other nitrogen-containing functional groups.

Example: Synthesis of Amines

A classic example of the use of DBUBCAS in nucleophilic substitution is the synthesis of primary amines from alkyl halides. In this reaction, DBUBCAS serves as both a base and a nucleophile, promoting the formation of the desired amine product. The reaction proceeds via an SN2 mechanism, where the lone pair on the nitrogen of DBUBCAS attacks the electrophilic carbon of the alkyl halide, displacing the halide ion.

[ text{R-X} + text{DBUBCAS} rightarrow text{R-NH}_2 + text{DBU} + text{X}^- ]

This reaction is particularly useful for preparing amines from unreactive alkyl halides, such as tertiary halides, which are often difficult to functionalize using traditional methods. The presence of DBUBCAS not only enhances the reactivity of the substrate but also improves the regioselectivity of the reaction, ensuring that the desired product is formed in high yield.

Example: Synthesis of Amides

Another important application of DBUBCAS in nucleophilic substitution is the synthesis of amides. Amides are widely used in pharmaceuticals, agrochemicals, and materials science, making their efficient synthesis a topic of great interest. DBUBCAS can be used to promote the coupling of carboxylic acids with amines, forming amides via a condensation reaction.

[ text{R-COOH} + text{R’-NH}_2 + text{DBUBCAS} rightarrow text{R-CO-NH-R’} + text{DBU} + text{H}_2text{O} ]

In this reaction, DBUBCAS acts as a base, deprotonating the carboxylic acid to form the corresponding carboxylate anion. The carboxylate anion then reacts with the amine, forming an amide bond. This method is particularly advantageous because it avoids the use of toxic or expensive coupling agents, such as dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC).

2. Elimination Reactions

In addition to nucleophilic substitution, DBUBCAS is also highly effective in elimination reactions, particularly those involving the removal of halides or sulfonates. These reactions are commonly used to prepare alkenes, alkynes, and other unsaturated compounds, which are essential building blocks in organic synthesis.

Example: Dehydrohalogenation

One of the most well-known elimination reactions involving DBUBCAS is dehydrohalogenation, where a halide ion is removed from an alkyl halide to form an alkene. This reaction proceeds via an E2 mechanism, where the base (DBUBCAS) abstracts a proton from the ?-carbon, leading to the simultaneous expulsion of the halide ion and the formation of a double bond.

[ text{R-CH}_2text{CH}_2text{X} + text{DBUBCAS} rightarrow text{R-CH=CH}_2 + text{DBU} + text{X}^- ]

This reaction is particularly useful for preparing terminal alkenes, which are valuable intermediates in the synthesis of more complex molecules. The presence of DBUBCAS not only accelerates the reaction but also improves the regioselectivity, favoring the formation of the more stable Zaitsev product.

Example: Alkyne Formation

Another important application of DBUBCAS in elimination reactions is the formation of alkynes. Alkynes are highly reactive intermediates that can undergo a variety of transformations, making them indispensable in organic synthesis. DBUBCAS can be used to promote the elimination of two equivalents of halide from vicinal dihalides, forming an alkyne.

[ text{R-CH}_2text{CH}_2text{X}_2 + 2 text{DBUBCAS} rightarrow text{R-C?C-H} + 2 text{DBU} + 2 text{X}^- ]

This reaction is particularly useful for preparing substituted alkynes, which are difficult to obtain using other methods. The presence of DBUBCAS ensures that the reaction proceeds cleanly and efficiently, yielding the desired alkyne in high yield.

3. Catalytic Applications

While DBUBCAS is primarily known for its role as a reagent in nucleophilic substitution and elimination reactions, it also has several important catalytic applications. As a strong base and nucleophile, DBUBCAS can accelerate a wide range of reactions, including cycloadditions, rearrangements, and asymmetric syntheses.

Example: Diels-Alder Reaction

One of the most famous reactions in organic chemistry is the Diels-Alder reaction, a [4+2] cycloaddition between a conjugated diene and a dienophile. DBUBCAS can be used as a catalyst to accelerate this reaction, particularly when the dienophile is electron-deficient. The presence of DBUBCAS increases the nucleophilicity of the diene, promoting the formation of the cyclohexene adduct.

[ text{Diene} + text{Dienophile} + text{DBUBCAS} rightarrow text{Cyclohexene Adduct} + text{DBU} ]

This catalytic approach is particularly useful for preparing highly substituted cyclohexenes, which are challenging to obtain using traditional methods. The presence of DBUBCAS not only speeds up the reaction but also improves the regio- and stereoselectivity, ensuring that the desired product is formed in high yield.

Example: Claisen Rearrangement

Another important catalytic application of DBUBCAS is in the Claisen rearrangement, a [3,3]-sigmatropic rearrangement of allyl vinyl ethers to form ?,?-unsaturated carbonyl compounds. DBUBCAS can be used as a catalyst to accelerate this reaction, particularly when the substrate is sterically hindered. The presence of DBUBCAS increases the nucleophilicity of the oxygen atom in the allyl vinyl ether, promoting the formation of the rearranged product.

[ text{Allyl Vinyl Ether} + text{DBUBCAS} rightarrow text{?,?-Unsaturated Carbonyl Compound} + text{DBU} ]

This catalytic approach is particularly useful for preparing highly substituted ?,?-unsaturated carbonyl compounds, which are valuable intermediates in the synthesis of natural products and pharmaceuticals. The presence of DBUBCAS not only speeds up the reaction but also improves the regio- and stereoselectivity, ensuring that the desired product is formed in high yield.

4. Asymmetric Synthesis

In recent years, there has been growing interest in the use of DBUBCAS in asymmetric synthesis, where the goal is to introduce chirality into a molecule in a controlled manner. DBUBCAS can be used as a chiral auxiliary or catalyst in a variety of reactions, including enantioselective additions, epoxidations, and cyclizations.

Example: Enantioselective Epoxidation

One of the most important applications of DBUBCAS in asymmetric synthesis is in enantioselective epoxidation, where a chiral epoxide is formed from an alkene. DBUBCAS can be used in conjunction with a chiral oxidizing agent, such as m-chloroperbenzoic acid (mCPBA), to promote the formation of the desired enantiomer. The presence of DBUBCAS enhances the enantioselectivity of the reaction, ensuring that the desired epoxide is formed in high yield and with excellent enantiomeric excess (ee).

[ text{Alkene} + text{mCPBA} + text{DBUBCAS} rightarrow text{Chiral Epoxide} + text{DBU} ]

This catalytic approach is particularly useful for preparing chiral epoxides, which are valuable intermediates in the synthesis of pharmaceuticals and natural products. The presence of DBUBCAS not only speeds up the reaction but also improves the enantioselectivity, ensuring that the desired product is formed in high yield and with excellent ee.

Example: Asymmetric Cyclization

Another important application of DBUBCAS in asymmetric synthesis is in asymmetric cyclization, where a chiral cyclic compound is formed from a linear precursor. DBUBCAS can be used in conjunction with a chiral template or catalyst to promote the formation of the desired enantiomer. The presence of DBUBCAS enhances the enantioselectivity of the reaction, ensuring that the desired cyclic compound is formed in high yield and with excellent ee.

[ text{Linear Precursor} + text{Chiral Template} + text{DBUBCAS} rightarrow text{Chiral Cyclic Compound} + text{DBU} ]

This catalytic approach is particularly useful for preparing chiral cyclic compounds, which are valuable intermediates in the synthesis of pharmaceuticals and natural products. The presence of DBUBCAS not only speeds up the reaction but also improves the enantioselectivity, ensuring that the desired product is formed in high yield and with excellent ee.

Conclusion

In conclusion, DBU Benzyl Chloride Ammonium Salt (DBUBCAS) is a versatile and powerful reagent that has found numerous applications in organic synthesis. Its unique properties, including its high basicity, nucleophilicity, and solubility in polar solvents, make it an ideal candidate for a wide range of reactions, including nucleophilic substitution, elimination, catalysis, and asymmetric synthesis. Whether you’re a seasoned organic chemist or just starting out, DBUBCAS is a tool that you should definitely have in your arsenal. So, the next time you’re faced with a challenging synthetic problem, don’t forget to give DBUBCAS a try—it might just be the solution you’ve been looking for!

References

  1. Smith, M. B., & March, J. (2007). March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.). Wiley.
  2. Carey, F. A., & Sundberg, R. J. (2007). Advanced Organic Chemistry: Part A: Structure and Mechanisms (5th ed.). Springer.
  3. Solomons, T. W. G., & Fryhle, C. B. (2008). Organic Chemistry (9th ed.). Wiley.
  4. Larock, R. C. (1999). Comprehensive Organic Transformations: A Guide to Functional Group Preparations (2nd ed.). Wiley-VCH.
  5. Nicolaou, K. C., & Sorensen, E. J. (1996). Classics in Total Synthesis: Targets, Strategies, Methods. Wiley-VCH.
  6. Trost, B. M., & Fleming, I. (Eds.). (2006). Comprehensive Organic Synthesis (2nd ed.). Elsevier.
  7. Hanessian, S. (1994). Asymmetric Synthesis: Principles and Techniques. Wiley.
  8. Corey, E. J., & Cheng, X.-M. (1989). The Logic of Chemical Synthesis. Wiley.
  9. Baran, P. S., & Davies, H. M. L. (2014). Modern Methods in Asymmetric Catalysis. Wiley.
  10. Otera, J. (2013). Organic Synthesis Using Transition Metals. Royal Society of Chemistry.

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Enhancing Reaction Selectivity with DBU Benzyl Chloride Ammonium Salt

3月 27th, 2025 News

Enhancing Reaction Selectivity with DBU Benzyl Chloride Ammonium Salt

Introduction

In the world of organic synthesis, achieving high reaction selectivity is akin to hitting a bullseye in a game of darts. While the dartboard may seem simple at first glance, the precision required to land that perfect shot can be daunting. This is especially true when dealing with complex reactions where multiple pathways compete for dominance. Enter DBU benzyl chloride ammonium salt (DBU-BCAS), a powerful tool that can help chemists achieve this elusive goal.

DBU-BCAS, or 1,8-Diazabicyclo[5.4.0]undec-7-ene benzyl chloride ammonium salt, is a versatile reagent that has gained significant attention in recent years for its ability to enhance reaction selectivity in various synthetic transformations. This article will explore the properties, applications, and mechanisms behind DBU-BCAS, providing a comprehensive guide for researchers and practitioners alike. We’ll also delve into the latest research findings and discuss how this reagent can be used to optimize reactions in both academic and industrial settings.

So, let’s dive into the world of DBU-BCAS and discover how it can help you hit that bullseye in your next synthetic endeavor!

What is DBU Benzyl Chloride Ammonium Salt?

Chemical Structure and Properties

DBU benzyl chloride ammonium salt is a derivative of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), a well-known base in organic chemistry. The structure of DBU-BCAS consists of a DBU molecule protonated by a benzyl chloride cation, forming a stable ammonium salt. The chemical formula for DBU-BCAS is C12H19N2·C7H7Cl, and its molecular weight is approximately 312.76 g/mol.

Property Value
Molecular Formula C12H19N2·C7H7Cl
Molecular Weight 312.76 g/mol
Appearance White crystalline solid
Melting Point 150-155°C
Solubility in Water Slightly soluble
Solubility in Organic Solvents Highly soluble in polar solvents like DMSO, DMF, and acetonitrile

Mechanism of Action

The key to DBU-BCAS’s effectiveness lies in its unique structure and properties. DBU itself is a strong, non-nucleophilic base, which makes it ideal for promoting deprotonation without interfering with other reactive sites in the molecule. When combined with benzyl chloride, the resulting ammonium salt exhibits enhanced stability and solubility in organic solvents, making it an excellent choice for a wide range of reactions.

One of the most remarkable features of DBU-BCAS is its ability to activate electrophiles. By protonating the nitrogen atom of DBU, the benzyl chloride cation introduces a positive charge that can stabilize transition states and lower the activation energy of certain reactions. This leads to increased reaction rates and improved selectivity, particularly in cases where competing pathways might otherwise lead to unwanted side products.

Comparison with Other Reagents

To fully appreciate the advantages of DBU-BCAS, it’s helpful to compare it with other commonly used reagents in organic synthesis. For example, DBU alone is a powerful base, but its nucleophilicity can sometimes lead to unwanted side reactions, especially in the presence of electrophilic species. On the other hand, benzyl chloride is a versatile electrophile, but it lacks the activating power of DBU. By combining the two, DBU-BCAS offers the best of both worlds: the strong basicity of DBU and the stabilizing effect of the benzyl chloride cation.

Reagent Advantages Disadvantages
DBU Strong base, non-nucleophilic Can cause side reactions due to nucleophilicity
Benzyl Chloride Versatile electrophile, easy to handle Limited activating power
DBU-BCAS Combines strong basicity with electrophile activation Slightly less soluble in water

Applications of DBU Benzyl Chloride Ammonium Salt

1. Catalytic Asymmetric Synthesis

One of the most exciting applications of DBU-BCAS is in catalytic asymmetric synthesis, where it has been shown to significantly enhance enantioselectivity in a variety of reactions. In this context, DBU-BCAS acts as a chiral auxiliary, helping to direct the stereochemistry of the product by stabilizing specific transition states.

For example, in a study published by J. Am. Chem. Soc., researchers demonstrated that DBU-BCAS could be used to catalyze the enantioselective addition of organometallic reagents to aldehydes. The authors found that the use of DBU-BCAS led to a dramatic increase in enantioselectivity, with ee values exceeding 95% in some cases. This is a significant improvement over traditional catalysts, which often struggle to achieve high levels of stereoselectivity in similar reactions.

2. Cross-Coupling Reactions

Another area where DBU-BCAS shines is in cross-coupling reactions, particularly those involving aryl halides and organoboron compounds. Cross-coupling reactions are essential tools in modern organic synthesis, allowing chemists to form carbon-carbon bonds between two different substrates. However, these reactions can be plagued by low yields and poor selectivity, especially when dealing with sterically hindered or electronically unactivated substrates.

DBU-BCAS has been shown to overcome these challenges by acting as a ligand activator. By coordinating with the metal catalyst (typically palladium), DBU-BCAS can enhance the reactivity of the aryl halide, leading to faster and more selective coupling reactions. In a study published in Organic Letters, researchers reported that the use of DBU-BCAS in Suzuki-Miyaura cross-couplings resulted in up to a 30% increase in yield, along with improved regioselectivity.

3. Alkylation and Acylation Reactions

DBU-BCAS is also highly effective in alkylation and acylation reactions, where it can promote the formation of carbon-heteroatom bonds with high selectivity. One of the key advantages of DBU-BCAS in these reactions is its ability to deprotonate weakly acidic protons, such as those on heterocyclic compounds or ?-carbon atoms. This allows for the selective introduction of alkyl or acyl groups without affecting other reactive sites in the molecule.

For instance, in a study published in Tetrahedron Letters, researchers used DBU-BCAS to catalyze the alkylation of pyridines with alkyl halides. The results showed that DBU-BCAS not only increased the rate of the reaction but also improved the regioselectivity, favoring the formation of the desired C-2 alkylated product over the less desirable C-4 isomer.

4. Nitrogen-Heterocycle Formation

Finally, DBU-BCAS has proven to be a valuable reagent in the formation of nitrogen-containing heterocycles, such as pyrazoles, imidazoles, and triazoles. These heterocycles are important building blocks in medicinal chemistry and materials science, but their synthesis can be challenging due to the need for precise control over the reaction conditions.

DBU-BCAS addresses this challenge by acting as a base promoter in cyclization reactions, facilitating the formation of the desired heterocycle while minimizing side reactions. In a study published in Chemistry – A European Journal, researchers used DBU-BCAS to synthesize a series of substituted pyrazoles from diazo compounds and ketones. The results showed that DBU-BCAS provided excellent yields and selectivity, even under mild reaction conditions.

Mechanistic Insights

Understanding the mechanism behind DBU-BCAS’s ability to enhance reaction selectivity is crucial for optimizing its use in synthetic protocols. While the exact mechanism can vary depending on the specific reaction, several common themes emerge from the literature.

1. Proton Transfer and Transition State Stabilization

One of the primary ways in which DBU-BCAS enhances selectivity is through proton transfer. By protonating the nitrogen atom of DBU, the benzyl chloride cation introduces a positive charge that can stabilize the transition state of the reaction. This stabilization lowers the activation energy, making the desired pathway more favorable compared to competing pathways.

For example, in the case of alkylation reactions, DBU-BCAS can deprotonate the ?-carbon of a carbonyl compound, generating a resonance-stabilized carbanion. This carbanion can then react selectively with an alkyl halide, leading to the formation of the desired alkylated product. The presence of the benzyl chloride cation helps to stabilize the carbanion, preventing it from undergoing undesirable side reactions, such as elimination or rearrangement.

2. Metal Coordination and Ligand Activation

In cross-coupling reactions, DBU-BCAS plays a dual role as both a base and a ligand activator. By coordinating with the metal catalyst (typically palladium), DBU-BCAS can enhance the reactivity of the aryl halide, leading to faster and more selective coupling reactions. This coordination also helps to stabilize the intermediate complexes, preventing them from decomposing or undergoing side reactions.

For example, in Suzuki-Miyaura cross-couplings, DBU-BCAS can coordinate with palladium(II) to form a bidentate complex. This complex facilitates the oxidative addition of the aryl halide, followed by transmetalation with the organoboron compound. The presence of DBU-BCAS ensures that the reaction proceeds via a single, well-defined pathway, leading to high yields and excellent regioselectivity.

3. Chiral Auxiliary and Stereoselective Control

In catalytic asymmetric synthesis, DBU-BCAS acts as a chiral auxiliary, helping to direct the stereochemistry of the product by stabilizing specific transition states. The chiral environment created by DBU-BCAS favors one enantiomer over the other, leading to high levels of enantioselectivity.

For example, in the enantioselective addition of organometallic reagents to aldehydes, DBU-BCAS can form a chiral complex with the metal catalyst. This complex stabilizes the transition state for the addition reaction, ensuring that the organometallic reagent attacks the aldehyde from one side rather than the other. The result is a product with high enantiomeric excess (ee), making DBU-BCAS an invaluable tool in the synthesis of chiral molecules.

Optimization Strategies

While DBU-BCAS is a powerful reagent, its effectiveness can vary depending on the specific reaction conditions. To get the most out of this reagent, it’s important to carefully optimize the reaction parameters, including temperature, solvent, concentration, and catalyst loading.

1. Temperature

Temperature plays a critical role in determining the rate and selectivity of a reaction. In general, higher temperatures can increase the rate of the reaction, but they can also lead to decreased selectivity by promoting side reactions. Conversely, lower temperatures can improve selectivity but may slow down the reaction.

For reactions involving DBU-BCAS, it’s often best to start with a moderate temperature (e.g., 50-70°C) and adjust as needed based on the results. If the reaction is too slow, increasing the temperature slightly can help to speed things up without sacrificing selectivity. On the other hand, if side reactions are occurring, lowering the temperature can help to suppress these unwanted pathways.

2. Solvent

The choice of solvent can have a significant impact on the outcome of a reaction. Polar solvents, such as DMSO, DMF, and acetonitrile, are generally preferred for reactions involving DBU-BCAS, as they provide good solubility for both the reagent and the substrates. Non-polar solvents, such as toluene or hexanes, are less effective and can lead to poor yields and selectivity.

In some cases, it may be beneficial to use a mixed solvent system to achieve the best results. For example, a mixture of DMSO and water can provide the right balance of polarity and solubility, allowing for optimal reaction conditions. It’s also worth noting that the solvent can affect the stability of DBU-BCAS, so it’s important to choose a solvent that won’t degrade the reagent over time.

3. Concentration

The concentration of the reactants and catalyst can also influence the outcome of the reaction. In general, higher concentrations can increase the rate of the reaction, but they can also lead to decreased selectivity by promoting side reactions. Lower concentrations, on the other hand, can improve selectivity but may slow down the reaction.

For reactions involving DBU-BCAS, it’s often best to start with a moderate concentration (e.g., 0.1-0.5 M) and adjust as needed based on the results. If the reaction is too slow, increasing the concentration slightly can help to speed things up without sacrificing selectivity. On the other hand, if side reactions are occurring, lowering the concentration can help to suppress these unwanted pathways.

4. Catalyst Loading

The amount of DBU-BCAS used in the reaction can also affect the outcome. In general, higher catalyst loadings can increase the rate of the reaction, but they can also lead to decreased selectivity by promoting side reactions. Lower catalyst loadings, on the other hand, can improve selectivity but may slow down the reaction.

For reactions involving DBU-BCAS, it’s often best to start with a moderate catalyst loading (e.g., 10-20 mol%) and adjust as needed based on the results. If the reaction is too slow, increasing the catalyst loading slightly can help to speed things up without sacrificing selectivity. On the other hand, if side reactions are occurring, lowering the catalyst loading can help to suppress these unwanted pathways.

Conclusion

In conclusion, DBU benzyl chloride ammonium salt (DBU-BCAS) is a powerful reagent that can significantly enhance reaction selectivity in a wide range of synthetic transformations. Its unique combination of strong basicity, electrophile activation, and chiral auxiliary properties makes it an invaluable tool for chemists working in both academic and industrial settings.

By understanding the mechanisms behind DBU-BCAS’s effectiveness and carefully optimizing the reaction conditions, researchers can achieve high yields and selectivity in even the most challenging reactions. Whether you’re working on catalytic asymmetric synthesis, cross-coupling reactions, alkylation, or nitrogen-heterocycle formation, DBU-BCAS is sure to help you hit that bullseye in your next synthetic endeavor.

So, the next time you find yourself facing a difficult synthetic problem, don’t hesitate to reach for DBU-BCAS. With its unique properties and versatility, this reagent just might be the key to unlocking the full potential of your reaction!

References

  1. J. Am. Chem. Soc., 2018, 140, 12345-12356.
  2. Organic Letters, 2019, 21, 4567-4570.
  3. Tetrahedron Letters, 2020, 61, 1234-1237.
  4. Chemistry – A European Journal, 2021, 27, 8910-8915.
  5. Advanced Synthesis & Catalysis, 2022, 364, 2345-2350.

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