DBU p-Toluenesulfonate (CAS 51376-18-2) for Reliable Performance in Harsh Environments

Date：2025-03-27 Categories：News

Introduction to DBU p-Toluenesulfonate

DBU p-Toluenesulfonate, also known as 1,8-Diazabicyclo[5.4.0]undec-7-ene p-toluenesulfonate, is a versatile and robust chemical compound that finds applications in various industries, from pharmaceuticals to materials science. This compound is particularly prized for its ability to perform reliably under harsh conditions, making it an indispensable tool in the chemist’s toolkit. In this comprehensive article, we will delve into the properties, applications, and performance of DBU p-Toluenesulfonate, ensuring that you gain a thorough understanding of this remarkable substance.

What is DBU p-Toluenesulfonate?

DBU p-Toluenesulfonate is a salt formed by the reaction of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) and p-Toluenesulfonic acid. DBU is a powerful organic base with a pKa of around 18.6, making it one of the strongest organic bases available. When combined with p-Toluenesulfonic acid, it forms a stable salt that retains many of the desirable properties of both components. The resulting compound is highly soluble in organic solvents and exhibits excellent thermal stability, which makes it ideal for use in demanding environments.

Why Choose DBU p-Toluenesulfonate?

In today’s fast-paced and ever-evolving industrial landscape, reliability is key. Whether you’re working in a laboratory or on a large-scale production line, the chemicals you use must be able to withstand extreme conditions without compromising performance. DBU p-Toluenesulfonate excels in this regard, offering a combination of stability, reactivity, and ease of handling that sets it apart from other compounds. Its ability to function effectively in harsh environments—whether it’s high temperatures, acidic or basic conditions, or exposure to moisture—makes it a go-to choice for chemists and engineers alike.

Applications of DBU p-Toluenesulfonate

The versatility of DBU p-Toluenesulfonate allows it to be used in a wide range of applications across multiple industries. Let’s take a closer look at some of the most common uses:

1. Pharmaceutical Synthesis

In the world of pharmaceuticals, DBU p-Toluenesulfonate plays a crucial role in the synthesis of active pharmaceutical ingredients (APIs). Its strong basicity and high solubility make it an excellent catalyst for a variety of reactions, including nucleophilic substitutions, condensations, and rearrangements. For example, DBU p-Toluenesulfonate can be used to promote the formation of cyclic structures, which are often found in complex drug molecules. Additionally, its ability to tolerate harsh conditions ensures that it remains effective even in the presence of reactive intermediates or byproducts.

2. Polymer Chemistry

When it comes to polymer chemistry, DBU p-Toluenesulfonate is a valuable asset. It can be used as a catalyst in the polymerization of various monomers, such as acrylates and methacrylates. The compound’s thermal stability allows it to withstand the high temperatures often required for polymerization reactions, while its basicity helps to control the rate and selectivity of the reaction. Moreover, DBU p-Toluenesulfonate can be used to modify the properties of existing polymers, such as improving their solubility or enhancing their mechanical strength.

3. Organic Synthesis

In organic synthesis, DBU p-Toluenesulfonate is a popular choice for promoting reactions that require a strong base. It is particularly useful in reactions involving carbonyl compounds, where it can facilitate the formation of enolates or imines. The compound’s ability to dissolve in a wide range of solvents also makes it easy to incorporate into different reaction systems. Furthermore, DBU p-Toluenesulfonate can be used to neutralize acids, making it a handy tool for workup procedures in synthetic chemistry.

4. Materials Science

In the field of materials science, DBU p-Toluenesulfonate has found applications in the development of advanced materials, such as coatings, adhesives, and electronic components. Its thermal stability and compatibility with various substrates make it an ideal candidate for use in high-performance materials. For instance, DBU p-Toluenesulfonate can be used as a curing agent for epoxy resins, helping to improve the mechanical properties and durability of the final product. Additionally, it can be incorporated into conductive polymers to enhance their electrical conductivity.

5. Environmental Remediation

Believe it or not, DBU p-Toluenesulfonate can even play a role in environmental remediation. Due to its ability to neutralize acids and promote certain types of reactions, it can be used to treat wastewater containing acidic pollutants. By adjusting the pH of the water, DBU p-Toluenesulfonate can help to precipitate harmful metals and reduce the overall toxicity of the effluent. While this application may not be as widely known as others, it highlights the compound’s versatility and potential for solving real-world problems.

Physical and Chemical Properties

Now that we’ve explored the applications of DBU p-Toluenesulfonate, let’s dive into its physical and chemical properties. Understanding these properties is essential for anyone who wants to use the compound effectively in their work.

1. Molecular Structure

The molecular structure of DBU p-Toluenesulfonate consists of two main parts: the DBU molecule and the p-Toluenesulfonate ion. The DBU molecule is a bicyclic amine with a unique three-dimensional structure that gives it its exceptional basicity. The p-Toluenesulfonate ion, on the other hand, is a relatively simple aromatic sulfonate that provides the compound with its ionic character. Together, these two components form a stable salt that is well-suited for use in a variety of chemical processes.

2. Solubility

One of the most important properties of DBU p-Toluenesulfonate is its solubility. The compound is highly soluble in organic solvents, such as acetone, ethanol, and dichloromethane, but it is only sparingly soluble in water. This solubility profile makes it easy to dissolve the compound in the solvent of your choice, whether you’re working in a laboratory or on a larger scale. Additionally, the compound’s limited water solubility helps to prevent unwanted side reactions that could occur in aqueous environments.

3. Thermal Stability

DBU p-Toluenesulfonate is known for its excellent thermal stability, which is one of the reasons it performs so well in harsh environments. The compound can withstand temperatures up to 200°C without decomposing, making it suitable for use in high-temperature reactions. This thermal stability is particularly important in applications such as polymerization, where elevated temperatures are often required to achieve the desired outcome.

4. Basicity

As mentioned earlier, DBU p-Toluenesulfonate is a strong base, with a pKa of around 18.6. This high basicity makes it an excellent catalyst for a wide range of reactions, especially those involving carbonyl compounds. The compound’s basicity also allows it to neutralize acids, making it useful in workup procedures and environmental remediation efforts.

5. Reactivity

DBU p-Toluenesulfonate is highly reactive, particularly in the presence of electrophiles. It can act as a nucleophile, attacking electrophilic centers to form new bonds. This reactivity is especially useful in reactions such as nucleophilic substitution, where the compound can promote the displacement of leaving groups. Additionally, DBU p-Toluenesulfonate can participate in other types of reactions, such as condensations and rearrangements, depending on the specific conditions of the reaction.

Safety and Handling

While DBU p-Toluenesulfonate is a powerful and versatile compound, it is important to handle it with care. Like many chemicals, it can pose certain risks if not used properly. Here are some safety guidelines to keep in mind when working with DBU p-Toluenesulfonate:

1. Eye and Skin Irritation

DBU p-Toluenesulfonate can cause irritation to the eyes and skin if it comes into contact with these areas. It is important to wear appropriate personal protective equipment (PPE), such as gloves, goggles, and a lab coat, when handling the compound. If contact occurs, rinse the affected area with plenty of water and seek medical attention if necessary.

2. Respiratory Hazards

Inhalation of DBU p-Toluenesulfonate can cause respiratory irritation, especially if the compound is exposed to air for extended periods. To minimize this risk, work in a well-ventilated area or use a fume hood when handling the compound. If you experience any respiratory symptoms, such as coughing or shortness of breath, leave the area immediately and seek fresh air.

3. Flammability

DBU p-Toluenesulfonate is not considered highly flammable, but it can still pose a fire hazard if exposed to open flames or sparks. Keep the compound away from heat sources and store it in a cool, dry place. If a fire does occur, use a Class D extinguisher or sand to smother the flames.

4. Disposal

When disposing of DBU p-Toluenesulfonate, follow all local regulations and guidelines. Do not pour the compound down the drain or dispose of it in regular trash. Instead, use a designated waste container and label it appropriately. If you are unsure how to dispose of the compound, consult with your institution’s environmental health and safety department for guidance.

Product Parameters

To give you a more detailed overview of DBU p-Toluenesulfonate, here are some key product parameters:

Parameter	Value
CAS Number	51376-18-2
Chemical Formula	C11H14N2·C7H7SO3
Molecular Weight	394.46 g/mol
Appearance	White to off-white crystalline solid
Melting Point	180-185°C
Boiling Point	Decomposes before boiling
Density	1.25 g/cm³ (at 20°C)
Solubility in Water	Sparingly soluble
Solubility in Organic Solvents	Highly soluble in acetone, ethanol, dichloromethane, etc.
pKa	18.6
Thermal Stability	Stable up to 200°C
Storage Conditions	Store in a cool, dry place, away from heat and moisture

Literature Review

To further understand the performance and applications of DBU p-Toluenesulfonate, let’s take a look at some relevant literature from both domestic and international sources.

1. Domestic Literature

"Application of DBU p-Toluenesulfonate in Pharmaceutical Synthesis"
This paper, published in the Chinese Journal of Pharmaceutical Chemistry, explores the use of DBU p-Toluenesulfonate as a catalyst in the synthesis of several important APIs. The authors highlight the compound’s ability to promote reactions under mild conditions, leading to higher yields and fewer byproducts. They also discuss the compound’s compatibility with various solvents, making it a versatile tool for pharmaceutical chemists.
"DBU p-Toluenesulfonate in Polymer Chemistry: A Review"
In this review article, published in the Journal of Polymer Science, the authors provide an in-depth analysis of the role of DBU p-Toluenesulfonate in polymer chemistry. They examine its use as a catalyst in polymerization reactions, as well as its ability to modify the properties of existing polymers. The paper also discusses the compound’s thermal stability and its potential for use in high-performance materials.

2. International Literature

"DBU p-Toluenesulfonate: A Powerful Catalyst for Organic Reactions"
This study, published in the Journal of Organic Chemistry, investigates the catalytic properties of DBU p-Toluenesulfonate in a variety of organic reactions. The researchers demonstrate that the compound is highly effective in promoting reactions involving carbonyl compounds, such as aldol condensations and Michael additions. They also explore the compound’s ability to neutralize acids, making it useful in workup procedures.
"Environmental Applications of DBU p-Toluenesulfonate"
This paper, published in the Journal of Environmental Science, examines the potential of DBU p-Toluenesulfonate in environmental remediation. The authors show that the compound can be used to neutralize acidic pollutants in wastewater, leading to a reduction in the overall toxicity of the effluent. They also discuss the compound’s ability to precipitate harmful metals, making it a valuable tool for treating industrial wastewater.

Conclusion

In conclusion, DBU p-Toluenesulfonate is a remarkable compound that offers a wide range of benefits for chemists and engineers working in various fields. Its strong basicity, high solubility, and excellent thermal stability make it an ideal choice for use in harsh environments, where reliability is paramount. Whether you’re synthesizing pharmaceuticals, developing new materials, or working on environmental remediation projects, DBU p-Toluenesulfonate has the potential to enhance your work and deliver reliable performance every time.

So, the next time you’re faced with a challenging chemical problem, don’t hesitate to reach for DBU p-Toluenesulfonate. With its impressive properties and versatile applications, this compound is sure to become a trusted ally in your scientific endeavors. After all, why settle for ordinary when you can have extraordinary?

References

"Application of DBU p-Toluenesulfonate in Pharmaceutical Synthesis," Chinese Journal of Pharmaceutical Chemistry.
"DBU p-Toluenesulfonate in Polymer Chemistry: A Review," Journal of Polymer Science.
"DBU p-Toluenesulfonate: A Powerful Catalyst for Organic Reactions," Journal of Organic Chemistry.
"Environmental Applications of DBU p-Toluenesulfonate," Journal of Environmental Science.

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