The leader of China special amines-

Archive for the category: News

Home / News

Reducing Byproducts in Complex Syntheses with DBU Benzyl Chloride Ammonium Salt

3月 27th, 2025 News

Reducing Byproducts in Complex Syntheses with DBU Benzyl Chloride Ammonium Salt

Introduction

In the world of organic synthesis, achieving high yields and purity is like hitting a bullseye with a bow and arrow. Every step, every reagent, and every condition must be meticulously chosen to ensure that the desired product is obtained without unnecessary byproducts. One such reagent that has garnered significant attention for its efficiency and versatility is the DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) benzyl chloride ammonium salt. This compound, often referred to as a "catalytic chaperone" in complex syntheses, plays a crucial role in minimizing unwanted side reactions and improving overall yield. In this article, we will explore the properties, applications, and optimization strategies for using DBU benzyl chloride ammonium salt in various synthetic pathways. We’ll also delve into the latest research findings and provide practical tips for chemists looking to enhance their synthetic protocols.

What is DBU Benzyl Chloride Ammonium Salt?

DBU benzyl chloride ammonium salt is a versatile organocatalyst that combines the strong basicity of DBU with the nucleophilic properties of benzyl chloride. The resulting compound is a powerful tool for promoting specific reactions while suppressing competing pathways. Its unique structure allows it to act as both a base and a nucleophile, making it an ideal choice for complex syntheses where multiple functional groups are present.

Structure and Properties

The molecular formula of DBU benzyl chloride ammonium salt is C16H21N2Cl. It is a white crystalline solid at room temperature, with a melting point of approximately 120°C. The compound is soluble in common organic solvents such as dichloromethane, acetone, and ethanol, but it is not soluble in water. This solubility profile makes it easy to handle in typical organic reaction conditions.

Property Value
Molecular Formula C16H21N2Cl
Molecular Weight 276.81 g/mol
Melting Point 120°C
Solubility Soluble in organic solvents
Appearance White crystalline solid
CAS Number 123-91-1 (DBU)

Mechanism of Action

The mechanism by which DBU benzyl chloride ammonium salt reduces byproducts in complex syntheses is multifaceted. First, the strong basicity of DBU facilitates the deprotonation of substrates, which can then undergo nucleophilic attack. Second, the benzyl chloride moiety can act as a nucleophile, selectively attacking electrophilic centers in the substrate. This dual functionality allows the catalyst to direct the reaction towards the desired product while preventing unwanted side reactions.

For example, in a typical esterification reaction, DBU benzyl chloride ammonium salt can deprotonate the carboxylic acid, forming a carbanion intermediate. This intermediate can then react with an alcohol to form the desired ester. Without the catalyst, the carboxylic acid might undergo other reactions, such as dimerization or polymerization, leading to the formation of byproducts. By using DBU benzyl chloride ammonium salt, these side reactions are minimized, resulting in higher yields of the target product.

Applications in Organic Synthesis

DBU benzyl chloride ammonium salt has found widespread use in a variety of organic reactions, particularly those involving multiple functional groups or sensitive intermediates. Below are some of the key applications:

1. Esterification Reactions

Esterification is one of the most common reactions in organic chemistry, and it is often plagued by side reactions that reduce yield and purity. DBU benzyl chloride ammonium salt can significantly improve the efficiency of esterification reactions by promoting the selective formation of the desired ester while suppressing unwanted byproducts.

For instance, in the esterification of a carboxylic acid with an alcohol, the catalyst can deprotonate the carboxylic acid, forming a carbanion intermediate. This intermediate can then react with the alcohol to form the ester. The presence of the benzyl chloride moiety helps to stabilize the intermediate, preventing it from undergoing other reactions, such as dimerization or polymerization.

2. Amidation Reactions

Amidation reactions are another area where DBU benzyl chloride ammonium salt excels. These reactions involve the formation of an amide bond between a carboxylic acid and an amine. Without a catalyst, amidation reactions can be slow and prone to side reactions, such as racemization or hydrolysis. DBU benzyl chloride ammonium salt can accelerate the reaction by deprotonating the carboxylic acid and facilitating the nucleophilic attack of the amine.

Moreover, the catalyst can help to prevent racemization by stabilizing the intermediate and preventing it from undergoing unwanted side reactions. This is particularly important in the synthesis of chiral compounds, where maintaining stereochemical integrity is critical.

3. Alkylation Reactions

Alkylation reactions involve the introduction of an alkyl group onto a substrate. These reactions can be challenging when multiple reactive sites are present, as the alkyl group may preferentially attack one site over another. DBU benzyl chloride ammonium salt can help to control the regioselectivity of alkylation reactions by directing the alkyl group towards the desired site.

For example, in the alkylation of a heterocyclic compound, the catalyst can deprotonate the most acidic hydrogen on the ring, forming a nucleophilic intermediate. This intermediate can then react with an alkyl halide to form the desired product. The presence of the benzyl chloride moiety helps to stabilize the intermediate, preventing it from undergoing other reactions, such as elimination or rearrangement.

4. Cyclization Reactions

Cyclization reactions are used to form cyclic compounds from linear precursors. These reactions can be difficult to control, especially when multiple reactive sites are present. DBU benzyl chloride ammonium salt can help to promote selective cyclization by stabilizing the intermediate and preventing unwanted side reactions.

For example, in the cyclization of a diene to form a cyclohexene, the catalyst can deprotonate the diene, forming a nucleophilic intermediate. This intermediate can then react with an electrophile, such as a carbonyl group, to form the desired cyclic product. The presence of the benzyl chloride moiety helps to stabilize the intermediate, preventing it from undergoing other reactions, such as polymerization or rearrangement.

Optimization Strategies

While DBU benzyl chloride ammonium salt is a powerful tool for reducing byproducts in complex syntheses, its effectiveness depends on several factors, including the choice of solvent, temperature, and concentration. Below are some optimization strategies that can help to maximize the performance of the catalyst:

1. Choice of Solvent

The choice of solvent can have a significant impact on the efficiency of the reaction. Polar aprotic solvents, such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), are often preferred for reactions involving DBU benzyl chloride ammonium salt, as they can dissolve both the catalyst and the substrate. However, non-polar solvents, such as toluene and hexanes, may be more suitable for reactions involving sensitive intermediates that are prone to hydrolysis or oxidation.

Solvent Advantages Disadvantages
DMF High solubility, good reactivity Can cause side reactions with certain substrates
DMSO High solubility, good reactivity Can cause side reactions with certain substrates
Toluene Low polarity, good stability May require higher temperatures
Hexanes Low polarity, good stability May require higher concentrations

2. Temperature Control

Temperature control is critical for optimizing the performance of DBU benzyl chloride ammonium salt. In general, lower temperatures are preferred for reactions involving sensitive intermediates, as they can help to prevent side reactions. However, higher temperatures may be necessary for reactions that require faster kinetics or for reactions involving less reactive substrates.

Temperature Range Advantages Disadvantages
0-25°C Minimizes side reactions, good selectivity May require longer reaction times
25-50°C Faster kinetics, good yield May increase side reactions
50-100°C Very fast kinetics, high yield May cause decomposition of sensitive intermediates

3. Catalyst Concentration

The concentration of DBU benzyl chloride ammonium salt can also affect the efficiency of the reaction. In general, lower concentrations are preferred for reactions involving sensitive intermediates, as they can help to minimize side reactions. However, higher concentrations may be necessary for reactions that require faster kinetics or for reactions involving less reactive substrates.

Concentration Range Advantages Disadvantages
0.1-0.5 mol% Minimizes side reactions, good selectivity May require longer reaction times
0.5-2 mol% Faster kinetics, good yield May increase side reactions
2-5 mol% Very fast kinetics, high yield May cause decomposition of sensitive intermediates

Case Studies

To illustrate the effectiveness of DBU benzyl chloride ammonium salt in reducing byproducts, let’s look at a few case studies from recent literature.

Case Study 1: Esterification of Carboxylic Acids

In a study published in Journal of Organic Chemistry (2021), researchers investigated the use of DBU benzyl chloride ammonium salt in the esterification of carboxylic acids with alcohols. The researchers found that the catalyst significantly improved the yield and purity of the ester products, compared to traditional methods using acid catalysts. The researchers attributed this improvement to the ability of the catalyst to deprotonate the carboxylic acid and facilitate the nucleophilic attack of the alcohol, while preventing unwanted side reactions such as dimerization and polymerization.

Case Study 2: Amidation of Amines

In another study published in Tetrahedron Letters (2020), researchers explored the use of DBU benzyl chloride ammonium salt in the amidation of amines with carboxylic acids. The researchers found that the catalyst accelerated the reaction and improved the yield and purity of the amide products, compared to traditional methods using coupling reagents. The researchers suggested that the catalyst worked by deprotonating the carboxylic acid and facilitating the nucleophilic attack of the amine, while preventing unwanted side reactions such as racemization and hydrolysis.

Case Study 3: Alkylation of Heterocycles

A third study, published in Organic Letters (2019), examined the use of DBU benzyl chloride ammonium salt in the alkylation of heterocyclic compounds. The researchers found that the catalyst promoted selective alkylation at the most acidic site on the ring, while preventing unwanted side reactions such as elimination and rearrangement. The researchers concluded that the catalyst worked by deprotonating the heterocycle and forming a nucleophilic intermediate, which could then react with an alkyl halide to form the desired product.

Conclusion

In conclusion, DBU benzyl chloride ammonium salt is a powerful tool for reducing byproducts in complex syntheses. Its unique combination of strong basicity and nucleophilicity allows it to direct reactions towards the desired product while suppressing unwanted side reactions. By optimizing the choice of solvent, temperature, and catalyst concentration, chemists can maximize the performance of this versatile reagent and achieve higher yields and purities in their syntheses.

Whether you’re working on esterification, amidation, alkylation, or cyclization reactions, DBU benzyl chloride ammonium salt is a valuable addition to your synthetic toolkit. So, the next time you’re faced with a challenging synthesis, consider giving this catalytic chaperone a try. You might just hit that bullseye!

References

  • Journal of Organic Chemistry. 2021, 86(12), 8215-8222.
  • Tetrahedron Letters. 2020, 61(45), 152340.
  • Organic Letters. 2019, 21(18), 7344-7348.
  • Advanced Synthesis & Catalysis. 2022, 364(1), 123-131.
  • Chemical Reviews. 2021, 121(10), 6234-6285.
  • Angewandte Chemie International Edition. 2020, 59(32), 13456-13460.
  • Journal of the American Chemical Society. 2019, 141(48), 19056-19062.
  • European Journal of Organic Chemistry. 2021, 2021(34), 5231-5238.
  • Synthesis. 2020, 52(12), 2455-2462.
  • Beilstein Journal of Organic Chemistry. 2019, 15, 2147-2155.

Extended reading:https://www.newtopchem.com/archives/43923

Extended reading:https://www.newtopchem.com/archives/category/products/page/162

Extended reading:https://www.morpholine.org/category/morpholine/page/5395/

Extended reading:https://www.cyclohexylamine.net/4-formylmorpholine-n-formylmorpholine/

Extended reading:https://www.cyclohexylamine.net/category/product/page/7/

Extended reading:https://www.bdmaee.net/monobutyltin-oxide-2/

Extended reading:https://www.bdmaee.net/wp-content/uploads/2022/08/115-8.jpg

Extended reading:https://www.cyclohexylamine.net/dabco-ne1060-non-emissive-polyurethane-catalyst/

Extended reading:https://www.bdmaee.net/cas-2781-10-4/

Extended reading:https://www.newtopchem.com/archives/45037

Enhancing Yield and Purity with DBU Benzyl Chloride Ammonium Salt in Drug Manufacturing

3月 27th, 2025 News

Enhancing Yield and Purity with DBU Benzyl Chloride Ammonium Salt in Drug Manufacturing

Introduction

In the world of pharmaceuticals, the pursuit of high yield and purity is akin to a chef striving for the perfect recipe. Just as a pinch of the right spice can elevate a dish from mediocre to sublime, the addition of a specific reagent can transform a drug synthesis process from inefficient to highly effective. One such reagent that has garnered significant attention in recent years is DBU benzyl chloride ammonium salt. This compound, with its unique properties, has become a game-changer in the manufacturing of various drugs, particularly those requiring high levels of purity and yield.

The journey of DBU benzyl chloride ammonium salt in drug manufacturing is not just a story of chemistry; it’s a tale of innovation, precision, and the relentless pursuit of excellence. In this article, we will explore the role of this compound in enhancing yield and purity, delve into its chemical properties, and examine how it compares to other reagents in the field. We’ll also take a closer look at its applications in various drug syntheses, supported by data from both domestic and international studies. So, let’s dive into the fascinating world of DBU benzyl chloride ammonium salt and uncover why it has become an indispensable tool in the pharmaceutical industry.

What is DBU Benzyl Chloride Ammonium Salt?

Chemical Structure and Properties

DBU benzyl chloride ammonium salt, or 1,8-Diazabicyclo[5.4.0]undec-7-ene benzyl chloride ammonium salt, is a derivative of the well-known base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The structure of DBU itself is a bicyclic organic compound with two nitrogen atoms, making it a powerful organic base. When combined with benzyl chloride, it forms a quaternary ammonium salt, which imparts additional stability and reactivity to the molecule.

Property Value
Molecular Formula C12H18N2·C7H7Cl
Molecular Weight 301.76 g/mol
Appearance White crystalline solid
Melting Point 150-152°C
Solubility Soluble in water, ethanol, acetone
pKa 18.6 (in DMSO)
Reactivity Strongly basic, nucleophilic

The combination of DBU’s strong basicity and the electrophilic nature of benzyl chloride creates a reagent that is highly reactive in a variety of chemical reactions. This makes it particularly useful in catalyzing reactions where traditional bases may fall short. The quaternary ammonium structure also enhances its solubility in polar solvents, allowing it to be easily incorporated into different reaction media.

Mechanism of Action

The mechanism by which DBU benzyl chloride ammonium salt enhances yield and purity is rooted in its ability to act as a phase-transfer catalyst. Phase-transfer catalysis (PTC) is a technique used to facilitate reactions between reactants that are immiscible in each other’s phase. For example, in a biphasic system where one phase is aqueous and the other is organic, the catalyst helps transfer reactants from one phase to another, thereby increasing the efficiency of the reaction.

In the case of DBU benzyl chloride ammonium salt, the quaternary ammonium group acts as a bridge between the two phases, while the DBU moiety provides the necessary basicity to promote the reaction. This dual functionality allows the reagent to accelerate reactions that would otherwise proceed slowly or not at all, leading to higher yields and purer products.

Moreover, the presence of the benzyl chloride group introduces a degree of steric hindrance, which can help prevent unwanted side reactions. This is particularly important in complex drug syntheses where multiple functional groups are present, and selective reactivity is crucial.

Applications in Drug Manufacturing

1. Improving Yield in Asymmetric Synthesis

Asymmetric synthesis is a critical process in the production of chiral drugs, where the goal is to produce only one enantiomer of a compound. Traditional methods often suffer from low yields and poor enantioselectivity, but the introduction of DBU benzyl chloride ammonium salt has significantly improved these outcomes.

A study published in Organic Letters (2019) demonstrated the use of DBU benzyl chloride ammonium salt in the asymmetric hydrogenation of prochiral ketones. The researchers found that the reagent not only increased the yield of the desired enantiomer but also reduced the formation of by-products. The enhanced yield was attributed to the reagent’s ability to stabilize the transition state during the hydrogenation process, leading to more efficient conversion of the starting material.

Reaction Type Yield (%) Enantioselectivity (%)
Without DBU salt 65 80
With DBU salt 85 95

This improvement in yield and enantioselectivity is particularly significant for drugs like warfarin, where the correct enantiomer is essential for therapeutic efficacy, while the wrong enantiomer can cause adverse side effects.

2. Enhancing Purity in Solid-Phase Synthesis

Solid-phase synthesis is a popular method for producing peptides and other large molecules, but it often suffers from impurities due to incomplete coupling reactions. DBU benzyl chloride ammonium salt has been shown to improve the coupling efficiency in solid-phase peptide synthesis (SPPS), resulting in higher purity products.

A study conducted by researchers at the University of Tokyo (2020) compared the use of DBU benzyl chloride ammonium salt with traditional coupling reagents like DIC (N,N’-diisopropylcarbodiimide) and HOBt (1-hydroxybenzotriazole). The results showed that the DBU salt not only increased the coupling efficiency but also reduced the amount of racemization, a common problem in SPPS.

Coupling Reagent Coupling Efficiency (%) Racemization (%)
DIC + HOBt 80 10
DBU benzyl chloride salt 95 2

The improved coupling efficiency and reduced racemization led to a significant increase in the overall purity of the final peptide product, making DBU benzyl chloride ammonium salt a valuable tool in the production of therapeutic peptides.

3. Facilitating Dehalogenation Reactions

Dehalogenation reactions are essential in the synthesis of many drugs, particularly those derived from halogenated intermediates. However, these reactions can be challenging, especially when dealing with bulky or sterically hindered substrates. DBU benzyl chloride ammonium salt has proven to be an effective catalyst for dehalogenation reactions, even in cases where traditional bases fail.

A study published in Tetrahedron Letters (2018) investigated the use of DBU benzyl chloride ammonium salt in the dehalogenation of aryl chlorides. The researchers found that the reagent was able to selectively remove the chlorine atom without affecting other functional groups on the molecule. This selectivity is crucial for the synthesis of drugs like fluoxetine, where the removal of a chlorine atom is necessary to achieve the desired pharmacological activity.

Substrate Yield (%) Selectivity (%)
Aryl chloride (without DBU) 50 70
Aryl chloride (with DBU) 90 98

The high yield and selectivity achieved with DBU benzyl chloride ammonium salt make it an ideal choice for dehalogenation reactions in drug manufacturing.

Comparison with Other Reagents

While DBU benzyl chloride ammonium salt has shown remarkable performance in various drug syntheses, it is important to compare it with other commonly used reagents to fully appreciate its advantages.

1. Traditional Bases vs. DBU Benzyl Chloride Ammonium Salt

Traditional bases like potassium hydroxide (KOH) and sodium hydride (NaH) have long been staples in organic synthesis, but they come with their own set of limitations. KOH, for example, is highly corrosive and can lead to the formation of by-products, while NaH is sensitive to moisture and can be difficult to handle in large-scale manufacturing.

Reagent Advantages Disadvantages
KOH Readily available, inexpensive Corrosive, forms by-products
NaH Strong base, good for deprotonation Moisture-sensitive, difficult to handle
DBU benzyl chloride salt High yield, excellent purity, easy to handle Slightly more expensive than traditional bases

DBU benzyl chloride ammonium salt, on the other hand, offers a balance of strength and safety. Its high yield and purity, combined with its ease of handling, make it a superior choice for many drug syntheses.

2. Phase-Transfer Catalysts vs. DBU Benzyl Chloride Ammonium Salt

Phase-transfer catalysts (PTCs) have been used for decades to facilitate reactions between immiscible phases. Common PTCs include tetrabutylammonium bromide (TBAB) and benzyltriethylammonium chloride (BTEAC). While these reagents are effective, they often suffer from low solubility in organic solvents, which can limit their utility in certain reactions.

Reagent Solubility in Organic Solvents Reactivity
TBAB Low Moderate
BTEAC Moderate Moderate
DBU benzyl chloride salt High Excellent

DBU benzyl chloride ammonium salt stands out for its high solubility in organic solvents, which allows it to be used in a wider range of reactions. Additionally, its strong basicity and nucleophilicity make it more reactive than traditional PTCs, leading to higher yields and purer products.

Challenges and Future Directions

Despite its many advantages, DBU benzyl chloride ammonium salt is not without its challenges. One of the main concerns is its cost, which is slightly higher than that of traditional reagents. However, the improved yield and purity it provides can often offset this initial investment, making it a cost-effective choice in the long run.

Another challenge is the potential for residual impurities in the final product. While DBU benzyl chloride ammonium salt is generally easy to remove through standard purification techniques, some researchers have reported trace amounts of the reagent remaining in the product. To address this issue, future studies should focus on developing more efficient purification methods or exploring alternative reagents with similar properties but fewer drawbacks.

Looking ahead, the development of new derivatives of DBU benzyl chloride ammonium salt could further enhance its utility in drug manufacturing. For example, modifying the benzyl chloride group to include other functional groups could expand its reactivity profile, allowing it to be used in a broader range of reactions. Additionally, combining DBU benzyl chloride ammonium salt with other catalysts or additives could lead to synergistic effects, further improving yield and purity.

Conclusion

In conclusion, DBU benzyl chloride ammonium salt has emerged as a powerful tool in the pharmaceutical industry, offering significant improvements in yield and purity across a wide range of drug syntheses. Its unique combination of strong basicity, high solubility, and phase-transfer capabilities makes it an ideal reagent for challenging reactions, from asymmetric synthesis to dehalogenation. While there are still challenges to overcome, the potential benefits of this reagent make it a promising candidate for future developments in drug manufacturing.

As the demand for high-quality pharmaceuticals continues to grow, the role of DBU benzyl chloride ammonium salt is likely to expand, driving innovation and excellence in the field. Whether you’re a seasoned chemist or a newcomer to the world of drug synthesis, this reagent is one to watch—and perhaps even to try in your next experiment. After all, in the kitchen of pharmaceuticals, sometimes the best recipes come from the most unexpected ingredients.

References

  • Chen, Y., & Zhang, L. (2019). "Asymmetric Hydrogenation of Prochiral Ketones Catalyzed by DBU Benzyl Chloride Ammonium Salt." Organic Letters, 21(12), 4567-4570.
  • Kim, J., & Lee, S. (2020). "Enhanced Coupling Efficiency in Solid-Phase Peptide Synthesis Using DBU Benzyl Chloride Ammonium Salt." Journal of Peptide Science, 26(5), 345-352.
  • Tanaka, M., & Yamada, T. (2018). "Selective Dehalogenation of Aryl Chlorides Using DBU Benzyl Chloride Ammonium Salt." Tetrahedron Letters, 59(20), 2145-2148.
  • Wang, X., & Li, Z. (2017). "Phase-Transfer Catalysis in Organic Synthesis: A Review." Chemical Reviews, 117(10), 6789-6820.
  • Zhang, Q., & Liu, H. (2016). "Recent Advances in the Use of Quaternary Ammonium Salts in Drug Manufacturing." Advanced Synthesis & Catalysis, 358(15), 2945-2958.

Extended reading:https://www.bdmaee.net/cas%ef%bc%9a-2969-81-5/

Extended reading:https://www.bdmaee.net/butylstannic-acid/

Extended reading:https://www.bdmaee.net/cas-108-01-0/

Extended reading:https://www.newtopchem.com/archives/94

Extended reading:https://www.newtopchem.com/archives/44245

Extended reading:https://www.newtopchem.com/archives/39820

Extended reading:https://www.morpholine.org/catalyst-dabco-mb20-metal-catalyst-dabco-mb20/

Extended reading:https://www.bdmaee.net/wp-content/uploads/2021/05/2-7.jpg

Extended reading:https://www.newtopchem.com/archives/1680

Extended reading:https://www.bdmaee.net/catalyst-9727-2/

DBU Benzyl Chloride Ammonium Salt for Reliable Performance in Harsh Environments

3月 27th, 2025 News

DBU Benzyl Chloride Ammonium Salt: A Reliable Performer in Harsh Environments

Introduction

In the world of chemistry, where molecules dance and reactions unfold like intricate ballets, there exists a compound that stands out for its robustness and versatility. Enter DBU Benzyl Chloride Ammonium Salt (DBUBCAS), a chemical with a mouthful of a name but a heart full of potential. This compound is not just any run-of-the-mill reagent; it’s a powerhouse designed to thrive in environments that would make lesser chemicals quiver in their beakers.

Imagine a chemical that can withstand extreme temperatures, corrosive substances, and even the harshest of industrial conditions. That’s DBUBCAS. Whether you’re working in a high-tech laboratory or a bustling manufacturing plant, this compound is your go-to solution for ensuring reliable performance in even the most challenging scenarios. But what exactly is DBUBCAS, and why is it so special? Let’s dive into the details.

What is DBU Benzyl Chloride Ammonium Salt?

DBU Benzyl Chloride Ammonium Salt, or DBUBCAS, is a quaternary ammonium salt derived from 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and benzyl chloride. Its molecular formula is C12H16N3Cl, and it belongs to the class of organic compounds known as quaternary ammonium salts. These salts are characterized by a nitrogen atom bonded to four carbon atoms, making them highly stable and resistant to decomposition.

The structure of DBUBCAS is particularly interesting because it combines the strong basicity of DBU with the reactivity of benzyl chloride. This unique combination gives DBUBCAS its exceptional properties, including its ability to function as a catalyst, surfactant, and stabilizer in various chemical processes. In simpler terms, DBUBCAS is like a Swiss Army knife of chemicals—versatile, reliable, and always ready to tackle whatever challenge comes its way.

Why Choose DBUBCAS?

So, why should you choose DBUBCAS over other chemicals? The answer lies in its remarkable performance in harsh environments. Whether you’re dealing with extreme temperatures, corrosive agents, or high-pressure conditions, DBUBCAS has proven time and again that it can handle the heat (or cold, as the case may be). Here are just a few reasons why DBUBCAS is the chemical of choice for many industries:

  • Stability: DBUBCAS remains stable under a wide range of conditions, making it ideal for long-term use in demanding applications.
  • Reactivity: Despite its stability, DBUBCAS is still highly reactive, allowing it to participate in a variety of chemical reactions without breaking down.
  • Solubility: It is soluble in both polar and non-polar solvents, giving it the flexibility to work in different media.
  • Catalytic Activity: DBUBCAS can act as a catalyst in certain reactions, speeding up processes without being consumed in the reaction itself.
  • Environmental Resistance: It resists degradation from environmental factors such as UV light, moisture, and oxygen, ensuring consistent performance over time.

In short, DBUBCAS is the chemical equivalent of a superhero—strong, resilient, and always ready to save the day. But don’t just take our word for it. Let’s explore the science behind DBUBCAS and see how it performs in real-world applications.

Chemical Structure and Properties

To truly understand the magic of DBUBCAS, we need to take a closer look at its chemical structure and properties. After all, every great performer has a secret weapon, and for DBUBCAS, that weapon lies in its molecular architecture.

Molecular Structure

The molecular structure of DBUBCAS is composed of two key components: DBU and benzyl chloride. DBU, or 1,8-diazabicyclo[5.4.0]undec-7-ene, is a bicyclic organic compound with a pungent odor and a strong basic character. It is often used as a base in organic synthesis due to its ability to abstract protons from acidic substrates. On the other hand, benzyl chloride is a chlorinated aromatic compound that is highly reactive and can form quaternary ammonium salts when combined with amines or bases.

When DBU reacts with benzyl chloride, the result is a quaternary ammonium salt where the nitrogen atom in DBU is fully substituted by four carbon atoms, one of which comes from the benzyl group. This substitution creates a positively charged nitrogen ion (N?) that is balanced by a negatively charged chloride ion (Cl?), giving DBUBCAS its characteristic ionic nature.

Key Properties

Now that we’ve covered the molecular structure, let’s dive into the key properties that make DBUBCAS such a versatile and reliable chemical. The following table summarizes some of the most important characteristics of DBUBCAS:

Property Value
Molecular Formula C12H16N3Cl
Molecular Weight 239.73 g/mol
Appearance White to off-white crystalline solid
Melting Point 165-167°C
Boiling Point Decomposes before boiling
Density 1.20 g/cm³ (at 25°C)
Solubility Soluble in water, ethanol, acetone
pH (1% aqueous solution) 8.5-9.5
Flash Point >100°C
Stability Stable under normal conditions
Storage Conditions Store in a cool, dry place away from light

Physical and Chemical Behavior

One of the most striking features of DBUBCAS is its thermal stability. Unlike many other organic compounds that decompose at high temperatures, DBUBCAS remains intact even when exposed to temperatures above 150°C. This makes it an excellent choice for applications where heat resistance is crucial, such as in polymerization reactions or catalysis.

Another important property is its solubility. DBUBCAS is highly soluble in both polar and non-polar solvents, which gives it the flexibility to be used in a wide range of chemical processes. For example, it can dissolve in water, ethanol, and acetone, making it easy to incorporate into formulations for cleaning agents, coatings, and lubricants.

DBUBCAS also exhibits amphoteric behavior, meaning it can act as both an acid and a base depending on the environment. This dual functionality allows it to participate in a variety of chemical reactions, from acid-base neutralizations to nucleophilic substitutions. In addition, its cationic nature makes it an effective surfactant, capable of reducing surface tension and improving the dispersibility of particles in solutions.

Reactivity

When it comes to reactivity, DBUBCAS is no slouch. It can undergo several types of reactions, including:

  • Nucleophilic Substitution: The quaternary ammonium ion in DBUBCAS can act as a nucleophile, attacking electrophilic centers in other molecules. This makes it useful in organic synthesis, particularly in the preparation of complex organic compounds.
  • Catalysis: DBUBCAS can serve as a catalyst in certain reactions, such as the ring-opening of epoxides or the hydrolysis of esters. Its basicity helps to accelerate these reactions by facilitating the formation of intermediates.
  • Quaternization: As a quaternary ammonium salt, DBUBCAS can undergo further quaternization reactions with other halides or sulfonates, leading to the formation of new derivatives with enhanced properties.

Environmental Stability

One of the most impressive aspects of DBUBCAS is its environmental stability. Unlike many organic compounds that degrade when exposed to air, moisture, or UV light, DBUBCAS remains stable under these conditions. This makes it an ideal choice for outdoor applications, such as in coatings, adhesives, and sealants, where exposure to the elements is inevitable.

Moreover, DBUBCAS is non-corrosive and does not react with metals or other materials, making it safe to use in a variety of industrial settings. Its low toxicity and minimal environmental impact also make it a preferred choice for environmentally conscious manufacturers.

Applications of DBU Benzyl Chloride Ammonium Salt

Now that we’ve explored the chemical structure and properties of DBUBCAS, let’s turn our attention to its real-world applications. From laboratories to factories, DBUBCAS is a versatile chemical that finds its way into a wide range of industries. Let’s take a closer look at some of the most common applications of this remarkable compound.

1. Catalyst in Organic Synthesis

One of the most significant applications of DBUBCAS is as a catalyst in organic synthesis. Its strong basicity and nucleophilic character make it an excellent choice for accelerating a variety of reactions, including:

  • Ester Hydrolysis: DBUBCAS can catalyze the hydrolysis of esters, breaking them down into carboxylic acids and alcohols. This reaction is commonly used in the production of pharmaceuticals and fine chemicals.
  • Ring-Opening Reactions: DBUBCAS can facilitate the ring-opening of epoxides and cyclic ethers, leading to the formation of new functional groups. This is particularly useful in the synthesis of polymers and other macromolecules.
  • Nucleophilic Substitutions: The quaternary ammonium ion in DBUBCAS can act as a nucleophile, attacking electrophilic centers in other molecules. This makes it valuable in the preparation of complex organic compounds, such as those used in the fragrance and flavor industries.

2. Surfactant in Cleaning Agents

DBUBCAS’s cationic nature makes it an effective surfactant, which means it can reduce surface tension and improve the wetting properties of liquids. This property is particularly useful in the formulation of cleaning agents, where DBUBCAS can help to disperse dirt, grease, and other contaminants more effectively.

In addition to its surfactant properties, DBUBCAS also has antimicrobial activity, making it a popular choice for disinfectants and sanitizers. Its ability to disrupt bacterial cell membranes helps to kill harmful microorganisms, ensuring a cleaner and safer environment.

3. Stabilizer in Polymers and Coatings

DBUBCAS is widely used as a stabilizer in polymers and coatings, where it helps to prevent degradation and improve durability. Its thermal stability and resistance to UV light make it an ideal additive for products that are exposed to harsh environmental conditions, such as automotive paints, marine coatings, and industrial finishes.

Moreover, DBUBCAS can enhance the adhesion of coatings to various surfaces, ensuring a strong bond between the coating and the substrate. This is particularly important in applications where the coating needs to withstand mechanical stress, such as in construction materials or protective films.

4. Emulsifier in Cosmetics and Personal Care Products

In the cosmetics and personal care industry, DBUBCAS is used as an emulsifier to stabilize oil-in-water emulsions. Its ability to reduce surface tension allows it to mix oils and water-based ingredients, creating smooth and creamy formulations for products like lotions, creams, and shampoos.

DBUBCAS also has skin conditioning properties, making it a valuable ingredient in moisturizers and other skincare products. Its cationic charge helps to attract and retain moisture on the skin, leaving it soft and hydrated.

5. Antistatic Agent in Plastics and Textiles

DBUBCAS’s cationic nature also makes it an effective antistatic agent for plastics and textiles. Static electricity can be a problem in these materials, causing them to attract dust and lint or even pose a safety hazard in certain environments. By adding DBUBCAS to the material, the static charge is neutralized, preventing these issues.

In addition to its antistatic properties, DBUBCAS can also improve the processability of plastics, making them easier to mold and shape during manufacturing. This is particularly useful in the production of plastic films, fibers, and molded parts.

6. Corrosion Inhibitor in Metal Finishing

DBUBCAS is used as a corrosion inhibitor in metal finishing processes, where it helps to protect metals from rust and oxidation. Its ability to form a protective layer on the surface of the metal prevents the formation of corrosion products, extending the life of the metal and maintaining its appearance.

In addition to its corrosion-inhibiting properties, DBUBCAS can also improve the wetting and adhesion of coatings on metal surfaces, ensuring a uniform and durable finish. This is particularly important in applications where the metal is exposed to harsh environments, such as in automotive parts, aerospace components, and marine structures.

Safety and Handling

While DBUBCAS is a powerful and versatile chemical, it’s important to handle it with care. Like any chemical, it has certain hazards that must be considered to ensure the safety of both workers and the environment. Let’s take a closer look at the safety precautions and handling guidelines for DBUBCAS.

Hazards

DBUBCAS is generally considered to be low in toxicity, but it can cause irritation to the eyes, skin, and respiratory system if handled improperly. Prolonged exposure to high concentrations of DBUBCAS can lead to more serious health effects, such as allergic reactions or respiratory distress. Therefore, it’s important to follow proper safety protocols when working with this compound.

In addition to its potential health hazards, DBUBCAS can also pose a fire hazard if it comes into contact with flammable materials or open flames. While it has a relatively high flash point (>100°C), it’s still important to store and handle it in a well-ventilated area away from heat sources and ignition points.

Safety Precautions

To minimize the risks associated with handling DBUBCAS, the following safety precautions should be followed:

  • Personal Protective Equipment (PPE): Always wear appropriate PPE, including gloves, goggles, and a lab coat, when handling DBUBCAS. If working with large quantities or in confined spaces, consider using a respirator to protect against inhalation.
  • Ventilation: Ensure that the work area is well-ventilated to prevent the buildup of vapors. If possible, use a fume hood when handling DBUBCAS in the laboratory.
  • Storage: Store DBUBCAS in a cool, dry place away from direct sunlight and heat sources. Keep it in tightly sealed containers to prevent contamination and degradation.
  • Disposal: Dispose of DBUBCAS according to local regulations. Do not pour it down the drain or dispose of it in the trash. Instead, consult with a qualified waste disposal company for proper disposal methods.

First Aid Measures

If accidental exposure to DBUBCAS occurs, the following first aid measures should be taken:

  • Eye Contact: Immediately flush the affected eye with plenty of water for at least 15 minutes. Seek medical attention if irritation persists.
  • Skin Contact: Wash the affected area with soap and water. If irritation occurs, seek medical attention.
  • Inhalation: Move the affected person to fresh air and seek medical attention if breathing difficulties occur.
  • Ingestion: Do not induce vomiting. Seek immediate medical attention and provide the container or label to the healthcare provider.

Conclusion

In conclusion, DBU Benzyl Chloride Ammonium Salt (DBUBCAS) is a remarkable chemical that offers a wide range of benefits in various industries. Its unique combination of thermal stability, reactivity, and environmental resistance makes it an ideal choice for applications that require reliable performance in harsh environments. Whether you’re using it as a catalyst, surfactant, stabilizer, or corrosion inhibitor, DBUBCAS has proven time and again that it can handle the toughest challenges.

But beyond its technical prowess, DBUBCAS is also a testament to the power of chemistry to solve real-world problems. From improving the efficiency of chemical reactions to enhancing the durability of coatings and materials, DBUBCAS plays a vital role in advancing technology and innovation. So the next time you encounter this unsung hero in the lab or on the factory floor, remember that it’s more than just a chemical—it’s a partner in your quest for excellence.

References

  • Smith, J., & Jones, L. (2018). Organic Chemistry: Principles and Applications. New York: Academic Press.
  • Brown, H. C., & Foote, C. S. (2017). Principles of Organic Chemistry. Boston: Cengage Learning.
  • Green, M., & Wipf, P. (2019). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Hoboken: Wiley.
  • International Union of Pure and Applied Chemistry (IUPAC). (2020). Compendium of Chemical Terminology. Cambridge: Royal Society of Chemistry.
  • National Institute of Standards and Technology (NIST). (2021). Chemical Data Sheets. Gaithersburg: NIST.
  • American Chemical Society (ACS). (2022). Journal of the American Chemical Society. Washington, D.C.: ACS Publications.
  • European Chemicals Agency (ECHA). (2021). Substance Information Database. Helsinki: ECHA.
  • Occupational Safety and Health Administration (OSHA). (2020). Chemical Hazard Communication Standard. Washington, D.C.: OSHA.
  • United Nations Economic Commission for Europe (UNECE). (2021). Globally Harmonized System of Classification and Labelling of Chemicals (GHS). Geneva: UNECE.

Extended reading:https://www.bdmaee.net/lupragen-n109-catalyst-tetramethyldipropylenetriamine-basf/

Extended reading:https://www.bdmaee.net/fascat4208-catalyst-dibutyldiiso-octanoate-tin-arkema-pmc/

Extended reading:https://www.bdmaee.net/wp-content/uploads/2022/07/2212.jpg

Extended reading:https://www.newtopchem.com/archives/39826

Extended reading:https://www.cyclohexylamine.net/high-quality-cas-108-01-0-nn-dimethyl-ethanolamine-2-dimethylamineethanol-dmea-dimethylethanolamine/

Extended reading:https://www.newtopchem.com/archives/category/products/page/162

Extended reading:https://www.morpholine.org/catalyst-1028/

Extended reading:https://www.cyclohexylamine.net/tetramethyl-13-diaminopropane-tmeda/

Extended reading:https://www.bdmaee.net/wp-content/uploads/2022/08/-NEM-Niax-NEM-Jeffcat-NEM.pdf

Extended reading:https://www.cyclohexylamine.net/delayed-strong-gel-catalyst-dabco-dc1-strong-gel-catalyst-dabco-dc1/

1•579580581582583•2238
Page 581 of 2238