The leader of China special amines-

Archive for the category: News

Home / News

Optimizing Thermal Stability with DBU Phenolate (CAS 57671-19-9)

3月 27th, 2025 News

Optimizing Thermal Stability with DBU Phenolate (CAS 57671-19-9)

Introduction

In the world of chemistry, stability is like a well-tuned symphony—every component must harmonize perfectly to achieve the desired outcome. When it comes to thermal stability, the stakes are even higher. Imagine a material that can withstand the heat of a blazing furnace without breaking a sweat; that’s the kind of performance we’re after. One compound that has been making waves in this domain is DBU Phenolate (CAS 57671-19-9). This versatile molecule, often referred to as 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, is a powerful ally in the quest for enhanced thermal stability.

But what exactly is DBU Phenolate, and why is it so special? In this article, we’ll dive deep into the world of DBU Phenolate, exploring its structure, properties, applications, and how it can be optimized for thermal stability. We’ll also take a look at some of the latest research and real-world examples where this compound has made a significant impact. So, buckle up and get ready for a journey through the fascinating world of chemical engineering!

What is DBU Phenolate?

Chemical Structure and Properties

DBU Phenolate, or 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, is a cyclic organic compound that belongs to the family of diazabicycloalkenes. Its molecular formula is C??H??N?O, and it has a molar mass of 243.32 g/mol. The structure of DBU Phenolate is characterized by a bicyclic ring system with two nitrogen atoms and a phenolate group attached to one of the carbons. This unique arrangement gives DBU Phenolate its remarkable properties, including:

  • High basicity: DBU Phenolate is one of the strongest organic bases available, with a pKa value of around 18.6. This makes it highly effective in catalyzing various reactions, especially those involving acid-base mechanisms.
  • Thermal stability: One of the most impressive features of DBU Phenolate is its ability to remain stable at high temperatures. Unlike many other organic compounds that degrade or decompose when exposed to heat, DBU Phenolate can withstand temperatures of up to 250°C without significant loss of functionality.
  • Solubility: DBU Phenolate is soluble in a wide range of organic solvents, including ethanol, methanol, and acetone. However, it is only sparingly soluble in water, which can be both an advantage and a limitation depending on the application.

Physical and Chemical Properties

To better understand the behavior of DBU Phenolate, let’s take a closer look at its physical and chemical properties. The following table summarizes some key characteristics:

Property Value
Molecular Formula C??H??N?O
Molar Mass 243.32 g/mol
Appearance White to off-white crystalline solid
Melting Point 150-155°C
Boiling Point Decomposes before boiling
Density 1.15 g/cm³ (at 20°C)
pKa 18.6
Solubility in Water Sparingly soluble
Solubility in Organic Solvents Soluble in ethanol, methanol, acetone
Thermal Stability Stable up to 250°C

Synthesis of DBU Phenolate

The synthesis of DBU Phenolate is a relatively straightforward process, though it requires careful control of reaction conditions to ensure high yields and purity. The most common method involves the reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with phenol in the presence of a suitable catalyst. The reaction proceeds via a nucleophilic substitution mechanism, where the phenolate ion displaces a proton from the DBU molecule.

The general reaction can be represented as follows:

[ text{DBU} + text{PhOH} rightarrow text{DBU Phenolate} + text{H}_2text{O} ]

This reaction is typically carried out at elevated temperatures (around 100-120°C) to facilitate the formation of the phenolate ion. The use of a base, such as potassium hydroxide (KOH), can help to increase the yield by promoting the deprotonation of phenol.

Applications of DBU Phenolate

Now that we’ve covered the basics of DBU Phenolate, let’s explore some of its most important applications. This versatile compound has found its way into a wide range of industries, from materials science to pharmaceuticals. Here are just a few examples:

1. Catalysis

One of the most prominent uses of DBU Phenolate is as a base catalyst in various chemical reactions. Its high basicity makes it particularly effective in promoting reactions that involve the deprotonation of acidic substrates. For instance, DBU Phenolate is commonly used in the synthesis of epoxides and lactones, where it catalyzes the ring-opening polymerization of cyclic esters and ethers.

In addition to its role in organic synthesis, DBU Phenolate has also been explored as a heterogeneous catalyst in industrial processes. By immobilizing DBU Phenolate on solid supports, such as silica or alumina, researchers have developed catalysts that can be easily recovered and reused, reducing waste and improving efficiency.

2. Polymer Science

DBU Phenolate plays a crucial role in the development of thermally stable polymers. Many polymers, especially those used in high-performance applications, require additives that can enhance their resistance to heat and degradation. DBU Phenolate serves as an excellent stabilizer in these systems, helping to prevent chain scission and cross-linking at elevated temperatures.

For example, in the production of polyurethanes, DBU Phenolate is often added to improve the thermal stability of the final product. Polyurethanes are widely used in automotive, construction, and electronics industries, where they are exposed to harsh environmental conditions. By incorporating DBU Phenolate, manufacturers can extend the service life of these materials and reduce the risk of failure under extreme temperatures.

3. Pharmaceuticals

In the pharmaceutical industry, DBU Phenolate has shown promise as a drug delivery agent. Its ability to form stable complexes with metal ions makes it an attractive candidate for developing metal-based drugs. These complexes can be designed to release the active ingredient in a controlled manner, improving the efficacy and safety of the treatment.

Moreover, DBU Phenolate has been investigated as a ligand in coordination chemistry, where it forms stable complexes with transition metals such as copper, zinc, and nickel. These complexes have potential applications in cancer therapy, as they can target specific cells and deliver therapeutic agents directly to the site of action.

4. Electronics and Semiconductors

The electronics industry is another area where DBU Phenolate has made significant contributions. In the fabrication of semiconductors and integrated circuits, thermal stability is critical to ensure the long-term performance of devices. DBU Phenolate has been used as an additive in the production of photoresists, which are light-sensitive materials used in photolithography. By enhancing the thermal stability of photoresists, DBU Phenolate helps to improve the resolution and accuracy of the patterning process, leading to smaller and more efficient electronic components.

Optimizing Thermal Stability with DBU Phenolate

While DBU Phenolate is already known for its excellent thermal stability, there are always ways to push the boundaries and achieve even better performance. In this section, we’ll explore some strategies for optimizing the thermal stability of DBU Phenolate, drawing on insights from both theoretical models and experimental studies.

1. Structural Modifications

One approach to enhancing the thermal stability of DBU Phenolate is to modify its molecular structure. By introducing substituents or altering the arrangement of functional groups, researchers can fine-tune the properties of the compound to better suit specific applications. For example, adding bulky groups to the phenolate ring can increase steric hindrance, making it more difficult for the molecule to undergo decomposition reactions at high temperatures.

Another strategy is to replace the phenolate group with other oxygen-containing functionalities, such as carboxylates or esters. These modifications can alter the electronic properties of the molecule, potentially improving its resistance to thermal degradation. However, care must be taken to ensure that the modified compound retains its basicity and catalytic activity, as these are essential for many of its applications.

2. Encapsulation and Immobilization

Encapsulating DBU Phenolate within a protective matrix can provide an additional layer of thermal protection. This technique has been successfully applied in the development of nanocomposites, where DBU Phenolate is embedded within a polymer or ceramic matrix. The encapsulating material acts as a barrier, preventing the diffusion of reactive species and slowing down the rate of decomposition.

Immobilization on solid supports, such as mesoporous silica or carbon nanotubes, is another effective way to enhance the thermal stability of DBU Phenolate. By anchoring the molecule to a stable surface, researchers can prevent it from aggregating or reacting with other components in the system. Moreover, immobilized DBU Phenolate can be easily separated from the reaction mixture, making it ideal for continuous-flow processes.

3. Synergistic Effects with Other Additives

Combining DBU Phenolate with other additives can lead to synergistic effects that further improve its thermal stability. For instance, antioxidants such as phenolic antioxidants or phosphites can work in tandem with DBU Phenolate to neutralize free radicals and prevent oxidative degradation. Similarly, metal chelators can form stable complexes with metal ions, reducing the likelihood of catalytic decomposition reactions.

In some cases, the addition of inorganic fillers such as clay or titanium dioxide can also enhance the thermal stability of DBU Phenolate. These fillers act as physical barriers, limiting the mobility of the molecule and protecting it from exposure to heat and oxygen.

4. Computational Modeling and Simulation

Advances in computational chemistry have opened up new possibilities for optimizing the thermal stability of DBU Phenolate. By using molecular dynamics simulations and quantum mechanical calculations, researchers can gain insights into the behavior of the molecule at the atomic level. These tools allow scientists to predict how different structural modifications or environmental conditions will affect the thermal stability of DBU Phenolate, enabling them to design more robust materials.

For example, a recent study by Smith et al. (2020) used density functional theory (DFT) to investigate the thermal decomposition pathways of DBU Phenolate. The results showed that the introduction of electron-withdrawing groups to the phenolate ring significantly increased the activation energy for decomposition, thereby improving the thermal stability of the compound. This finding highlights the power of computational modeling in guiding experimental efforts to optimize the performance of DBU Phenolate.

Case Studies and Real-World Applications

To illustrate the practical benefits of DBU Phenolate in enhancing thermal stability, let’s take a look at a few case studies from various industries.

1. Automotive Industry: Thermally Stable Coatings

In the automotive sector, coatings play a vital role in protecting vehicles from environmental damage. However, traditional coatings often struggle to maintain their integrity at high temperatures, leading to cracking, peeling, and discoloration. To address this challenge, a leading coatings manufacturer developed a new formulation that incorporates DBU Phenolate as a stabilizer.

The addition of DBU Phenolate significantly improved the thermal stability of the coating, allowing it to withstand temperatures of up to 200°C without degradation. This breakthrough enabled the company to produce coatings that offer superior protection for engines, exhaust systems, and other high-temperature components. As a result, the manufacturer saw a significant reduction in warranty claims and customer complaints, leading to increased market share and profitability.

2. Electronics: High-Performance Photoresists

As mentioned earlier, DBU Phenolate has found widespread use in the electronics industry, particularly in the production of photoresists for semiconductor manufacturing. A major challenge in this field is the need to balance thermal stability with sensitivity to light. Too much thermal stability can make the photoresist resistant to patterning, while too little can lead to premature decomposition during processing.

A team of researchers at a leading semiconductor company tackled this issue by developing a novel photoresist formulation that includes DBU Phenolate as a thermal stabilizer. Through careful optimization of the molecular structure and processing conditions, they were able to create a photoresist that exhibits excellent thermal stability while maintaining high sensitivity to ultraviolet (UV) light. This innovation has enabled the production of smaller, faster, and more reliable electronic devices, driving advancements in fields such as artificial intelligence, telecommunications, and consumer electronics.

3. Pharmaceuticals: Controlled Drug Delivery

In the pharmaceutical industry, DBU Phenolate has been explored as a ligand for developing metal-based drugs with improved thermal stability. One notable example is the development of a copper(II)-based anticancer drug that uses DBU Phenolate as a stabilizing agent. The complex formed between copper(II) and DBU Phenolate is highly stable at physiological temperatures, ensuring that the drug remains intact until it reaches the target site.

Clinical trials have shown that this new formulation is more effective than traditional copper-based drugs, with fewer side effects and a longer half-life in the bloodstream. The enhanced thermal stability of the complex allows for more precise control over the release of the active ingredient, leading to better treatment outcomes for patients.

Conclusion

In conclusion, DBU Phenolate (CAS 57671-19-9) is a remarkable compound with a wide range of applications in various industries. Its exceptional thermal stability, combined with its high basicity and versatility, makes it an invaluable tool for chemists and engineers alike. Whether you’re working on advanced materials, pharmaceuticals, or electronics, DBU Phenolate offers a powerful solution for enhancing the performance of your products.

By exploring strategies such as structural modifications, encapsulation, synergistic effects with other additives, and computational modeling, researchers can continue to push the boundaries of what’s possible with DBU Phenolate. As we move forward into an era of increasingly demanding technological challenges, this versatile compound will undoubtedly play a key role in shaping the future of thermal stability and beyond.

References

  • Smith, J., et al. (2020). "Thermal Decomposition Pathways of DBU Phenolate: A Density Functional Theory Study." Journal of Physical Chemistry A, 124(12), 2456-2464.
  • Zhang, L., et al. (2018). "Enhancing the Thermal Stability of Polyurethanes with DBU Phenolate Additives." Polymer Engineering & Science, 58(5), 678-685.
  • Wang, X., et al. (2019). "DBU Phenolate as a Ligand for Copper-Based Anticancer Drugs: Synthesis, Characterization, and Biological Evaluation." Journal of Medicinal Chemistry, 62(10), 5123-5132.
  • Brown, M., et al. (2021). "Thermally Stable Coatings for Automotive Applications: The Role of DBU Phenolate." Surface and Coatings Technology, 401, 126458.
  • Lee, S., et al. (2020). "High-Performance Photoresists for Semiconductor Manufacturing: The Impact of DBU Phenolate on Thermal Stability and UV Sensitivity." Journal of Photopolymer Science and Technology, 33(4), 457-464.

Extended reading:https://www.bdmaee.net/wp-content/uploads/2022/08/Polyurethane-rigid-foam-catalyst-CAS15875-13-5-Jeffcat-TR-90.pdf

Extended reading:https://www.newtopchem.com/archives/45137

Extended reading:https://www.cyclohexylamine.net/triethylenediamine-cas-280-57-9/

Extended reading:https://www.newtopchem.com/archives/category/products/page/62

Extended reading:https://www.bdmaee.net/cas-616-47-7/

Extended reading:https://www.newtopchem.com/archives/category/products/page/133

Extended reading:https://www.newtopchem.com/archives/39802

Extended reading:https://www.newtopchem.com/archives/43960

Extended reading:https://www.newtopchem.com/archives/category/products/page/8

Extended reading:https://www.newtopchem.com/archives/40466

DBU Phthalate (CAS 97884-98-5) for Reliable Performance in Extreme Conditions

3月 27th, 2025 News

DBU Phthalate (CAS 97884-98-5): Reliable Performance in Extreme Conditions

Introduction

In the world of chemistry, certain compounds stand out for their exceptional performance under extreme conditions. One such compound is DBU Phthalate, also known by its CAS number 97884-98-5. This versatile chemical has found its way into a variety of industries, from pharmaceuticals to coatings, thanks to its unique properties and reliability. In this comprehensive guide, we will delve deep into the world of DBU Phthalate, exploring its structure, applications, safety considerations, and much more. So, buckle up and join us on this fascinating journey!

What is DBU Phthalate?

DBU Phthalate, or 1,8-Diazabicyclo[5.4.0]undec-7-ene phthalate, is an organic compound that belongs to the class of phthalates. It is derived from DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a powerful base used in organic synthesis, and phthalic acid, a common building block in the production of plasticizers. The combination of these two components results in a compound with remarkable stability and reactivity, making it a valuable asset in various industrial processes.

Chemical Structure

The molecular formula of DBU Phthalate is C23H22N2O4, and its molecular weight is approximately 398.43 g/mol. The compound features a bicyclic ring system with a nitrogen atom at positions 1 and 8, which gives it its characteristic basicity. The phthalate group, consisting of two benzene rings connected by a carboxylate ester, provides additional stability and solubility in organic solvents.

Property Value
Molecular Formula C??H??N?O?
Molecular Weight 398.43 g/mol
Appearance White to off-white solid
Melting Point 160-165°C
Boiling Point Decomposes before boiling
Solubility Soluble in organic solvents, insoluble in water
Density 1.25 g/cm³

Synthesis of DBU Phthalate

The synthesis of DBU Phthalate typically involves the reaction between DBU and phthalic anhydride in the presence of a suitable solvent. The reaction proceeds via nucleophilic addition, where the nitrogen atoms of DBU attack the carbonyl groups of phthalic anhydride, forming the phthalate ester. This process is relatively straightforward and can be carried out under mild conditions, making it an attractive option for large-scale production.

Physical and Chemical Properties

DBU Phthalate is a white to off-white solid with a melting point ranging from 160 to 165°C. It is highly soluble in organic solvents such as acetone, ethanol, and dichloromethane but is insoluble in water. This property makes it ideal for use in non-aqueous systems, where water sensitivity could be a concern. Additionally, DBU Phthalate exhibits excellent thermal stability, making it suitable for applications that require exposure to high temperatures.

Property Description
Appearance White to off-white solid
Odor Odorless
Stability Stable under normal conditions
Reactivity Reacts with acids, halides, and electrophiles
Toxicity Low toxicity in small quantities

Applications of DBU Phthalate

DBU Phthalate’s unique combination of properties makes it a versatile compound with a wide range of applications across various industries. Let’s explore some of the key areas where this compound shines.

1. Pharmaceutical Industry

In the pharmaceutical sector, DBU Phthalate is used as an intermediate in the synthesis of drugs and APIs (Active Pharmaceutical Ingredients). Its ability to act as a protecting group for functional groups like amines and alcohols makes it invaluable in multi-step syntheses. For example, DBU Phthalate can be used to temporarily mask an amine group during a reaction, preventing unwanted side reactions and ensuring the desired product is formed.

Additionally, DBU Phthalate has been explored as a potential prodrug carrier. Prodrugs are inactive compounds that are converted into active drugs within the body, often improving the bioavailability and efficacy of the medication. By attaching DBU Phthalate to a drug molecule, researchers can control the release of the active compound, leading to better therapeutic outcomes.

2. Coatings and Polymers

One of the most significant applications of DBU Phthalate is in the formulation of coatings and polymers. The compound acts as a plasticizer, improving the flexibility and durability of materials like PVC (Polyvinyl Chloride). Plasticizers are essential in reducing the brittleness of polymers, allowing them to withstand mechanical stress without cracking or breaking.

Moreover, DBU Phthalate enhances the adhesion properties of coatings, making them more resistant to peeling and flaking. This is particularly important in industries such as automotive, construction, and electronics, where long-lasting and durable coatings are critical. The compound’s ability to remain stable under extreme temperatures and UV exposure further adds to its appeal in these applications.

3. Catalysis

DBU Phthalate plays a crucial role in catalysis, especially in organic synthesis. As a derivative of DBU, it retains the strong basicity of its parent compound, making it an excellent catalyst for various reactions, including Michael additions, aldol condensations, and Diels-Alder reactions. The phthalate group provides additional stability, allowing the catalyst to remain active even under harsh conditions.

In recent years, DBU Phthalate has gained attention as a green catalyst, offering a more environmentally friendly alternative to traditional metal-based catalysts. Its ability to promote reactions without the need for toxic metals or harsh solvents makes it an attractive option for sustainable chemistry.

4. Dye and Pigment Industry

The dye and pigment industry relies heavily on chemicals that can enhance the colorfastness and stability of dyes. DBU Phthalate is used as a mordant, a substance that helps fix dyes to fabrics and other materials. By forming a complex with the dye molecules, DBU Phthalate prevents them from washing out or fading over time.

In addition to its mordant properties, DBU Phthalate can also be used as a dispersing agent for pigments. This ensures that the pigments are evenly distributed throughout the medium, resulting in vibrant and uniform colors. The compound’s compatibility with both organic and inorganic pigments makes it a versatile choice for a wide range of applications, from textiles to paints.

5. Electronics and Semiconductors

In the electronics industry, DBU Phthalate is used in the production of photoresists, which are light-sensitive materials used in semiconductor manufacturing. Photoresists are essential for creating intricate patterns on silicon wafers, allowing for the precise placement of transistors and other components. DBU Phthalate improves the resolution and sensitivity of photoresists, enabling the fabrication of smaller and more efficient electronic devices.

Furthermore, DBU Phthalate is used as a dopant in the production of organic semiconductors. By introducing impurities into the semiconductor material, dopants can alter its electrical properties, making it more conductive or insulating as needed. This is particularly important in the development of next-generation flexible electronics and organic solar cells.

Safety Considerations

While DBU Phthalate offers numerous benefits, it is important to handle this compound with care. Like many phthalates, DBU Phthalate has raised concerns about its potential impact on human health and the environment. However, studies have shown that the compound has low toxicity when used in small quantities and under controlled conditions.

1. Health Hazards

Prolonged exposure to DBU Phthalate can cause irritation to the eyes, skin, and respiratory system. Ingestion of large amounts may lead to gastrointestinal distress, although this is unlikely in most industrial settings. To minimize the risk of exposure, it is recommended to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a respirator when handling the compound.

2. Environmental Impact

Phthalates, including DBU Phthalate, have been linked to environmental pollution, particularly in aquatic ecosystems. These compounds can leach into water sources, affecting wildlife and potentially entering the food chain. To mitigate this issue, manufacturers are encouraged to adopt best practices for waste management and disposal, ensuring that DBU Phthalate does not enter the environment.

3. Regulatory Status

Several regulatory bodies have established guidelines for the use of phthalates, including DBU Phthalate. In the European Union, for example, the REACH (Registration, Evaluation, Authorization, and Restriction of Chemicals) regulation requires companies to provide detailed information on the safety and environmental impact of their products. Similarly, the U.S. Environmental Protection Agency (EPA) has set limits on the permissible levels of phthalates in consumer products.

Future Prospects

As research into DBU Phthalate continues, new applications and improvements are likely to emerge. One area of interest is the development of more sustainable and eco-friendly formulations. Scientists are exploring ways to reduce the environmental impact of phthalates while maintaining their desirable properties. For example, biodegradable alternatives to traditional phthalates are being investigated, offering a greener solution for industries that rely on these compounds.

Another exciting prospect is the use of DBU Phthalate in advanced materials science. Researchers are investigating its potential as a component in smart materials, which can respond to external stimuli such as temperature, light, or pH changes. These materials have a wide range of applications, from self-healing coatings to responsive drug delivery systems.

Conclusion

DBU Phthalate (CAS 97884-98-5) is a remarkable compound that has proven its worth in a variety of industries. From pharmaceuticals to electronics, its unique properties make it an indispensable tool for chemists and engineers alike. While safety considerations must be taken into account, the benefits of DBU Phthalate far outweigh the risks when used responsibly. As research continues to uncover new applications and improvements, this versatile compound is sure to play an increasingly important role in the future of chemistry.

References

  1. Smith, J. A., & Brown, L. M. (2015). Phthalates: Chemistry, Applications, and Environmental Impact. Springer.
  2. Johnson, R. E., & Williams, P. T. (2018). Organic Synthesis: Principles and Practice. Wiley.
  3. Chen, X., & Zhang, Y. (2020). Green Chemistry and Sustainable Development. Elsevier.
  4. Patel, D. K., & Kumar, A. (2019). Pharmaceutical Excipients: Properties and Applications. CRC Press.
  5. Lee, S. H., & Kim, J. (2021). Advanced Materials for Electronics and Optoelectronics. Taylor & Francis.
  6. Thompson, M. J., & Davis, C. L. (2017). Environmental Toxicology of Phthalates. Oxford University Press.
  7. Wang, L., & Li, Z. (2016). Polymer Science and Engineering. Academic Press.
  8. Gupta, V. K., & Singh, R. P. (2019). Catalysis in Organic Synthesis. Springer.
  9. Zhang, W., & Liu, H. (2020). Dye and Pigment Chemistry. John Wiley & Sons.
  10. Tanaka, K., & Sato, T. (2018). Semiconductor Manufacturing Technology. McGraw-Hill Education.

We hope you’ve enjoyed this comprehensive exploration of DBU Phthalate! Whether you’re a seasoned chemist or just curious about the world of organic compounds, this guide should provide you with a solid understanding of what makes DBU Phthalate so special. If you have any questions or would like to dive deeper into any of the topics covered here, feel free to reach out. Happy experimenting! 🧪

Extended reading:https://www.newtopchem.com/archives/1763

Extended reading:https://www.bdmaee.net/dabco-r-8020-jeffcat-td-20-teda-a20/

Extended reading:https://www.bdmaee.net/spraying-composite-amine-catalyst/

Extended reading:https://www.bdmaee.net/wp-content/uploads/2022/08/Butyl-tin-thiolate-10584-98-2-CAS-10584-98-2-Butyltin-mercaptide.pdf

Extended reading:https://www.bdmaee.net/dabco-ne210-balance-catalyst-ne210-dabco-amine-catalyst/

Extended reading:https://www.newtopchem.com/archives/44014

Extended reading:https://www.bdmaee.net/spraying-composite-amine-catalyst-nt-cat-pt1003-pt1003/

Extended reading:https://www.newtopchem.com/archives/100

Extended reading:https://www.newtopchem.com/archives/1888

Extended reading:https://www.bdmaee.net/pc5-catalyst/

Applications of DBU Phenolate (CAS 57671-19-9) in Biochemical Research

3月 27th, 2025 News

Applications of DBU Phenolate (CAS 57671-19-9) in Biochemical Research

Introduction

In the world of biochemical research, finding the right tools can often feel like searching for a needle in a haystack. One such tool that has gained significant attention is DBU Phenolate (CAS 57671-19-9). This compound, with its unique properties and versatile applications, has become an indispensable ally for researchers working in various fields, from enzyme catalysis to drug discovery. In this article, we will explore the fascinating world of DBU Phenolate, delving into its structure, properties, and diverse applications in biochemical research. So, buckle up and join us on this journey as we uncover the secrets of this remarkable compound!

What is DBU Phenolate?

DBU Phenolate, also known as 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, is a derivative of the powerful base DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene). The addition of a phenolate group to DBU significantly alters its chemical behavior, making it a valuable reagent in organic synthesis and biochemical studies.

Chemical Structure and Properties

DBU Phenolate has a molecular formula of C12H17N2O and a molecular weight of 203.28 g/mol. Its structure consists of a bicyclic ring system with two nitrogen atoms and a phenolate group attached to one of the nitrogen atoms. This unique arrangement gives DBU Phenolate several interesting properties:

  • High Basicity: DBU Phenolate is a strong base, capable of deprotonating even weak acids. This property makes it an excellent catalyst for acid-catalyzed reactions.
  • Nucleophilicity: The presence of the phenolate group enhances the nucleophilic character of the molecule, allowing it to participate in various substitution and addition reactions.
  • Solubility: DBU Phenolate is soluble in polar solvents such as water, ethanol, and DMSO, making it easy to handle in laboratory settings.
  • Stability: Unlike some other strong bases, DBU Phenolate is relatively stable under ambient conditions, which adds to its appeal as a reagent.

Product Parameters

To better understand the characteristics of DBU Phenolate, let’s take a closer look at its key parameters:

Parameter Value
Molecular Formula C12H17N2O
Molecular Weight 203.28 g/mol
Appearance White crystalline solid
Melting Point 150-152°C
Boiling Point Decomposes before boiling
Solubility Soluble in water, ethanol, DMSO
pKa ~18 (in DMSO)
Storage Conditions Dry, cool, and dark place
Shelf Life 2 years (when stored properly)

Synthesis of DBU Phenolate

The synthesis of DBU Phenolate is a straightforward process that involves the reaction of DBU with phenol in the presence of a base. The general procedure is as follows:

  1. Preparation of DBU: DBU can be synthesized by the cycloaddition of 1,5-diazacycloheptatriene and acrolein. Alternatively, it can be purchased commercially.
  2. Reaction with Phenol: In a typical synthesis, DBU is dissolved in a polar solvent such as DMSO or ethanol. Phenol is then added to the solution, followed by a strong base like potassium hydroxide (KOH) or sodium hydride (NaH). The reaction proceeds via a nucleophilic substitution mechanism, where the phenolate ion attacks the electrophilic nitrogen atom of DBU.
  3. Isolation and Purification: After the reaction is complete, the product is isolated by filtration or precipitation. It can be further purified by recrystallization or column chromatography.

Applications in Biochemical Research

Now that we have a good understanding of what DBU Phenolate is and how it is made, let’s dive into its applications in biochemical research. The versatility of this compound makes it suitable for a wide range of studies, from basic enzymology to advanced drug development.

1. Enzyme Catalysis

Enzymes are biological catalysts that play a crucial role in almost every cellular process. Understanding how enzymes work and how they can be manipulated is a central goal of biochemical research. DBU Phenolate has found several applications in the study of enzyme catalysis, particularly in the field of enzyme inhibition.

Mechanism-Based Inhibition

One of the most exciting applications of DBU Phenolate is its use as a mechanism-based inhibitor of serine proteases. Serine proteases are a class of enzymes that cleave peptide bonds in proteins. They play important roles in digestion, blood clotting, and immune responses. However, excessive activity of these enzymes can lead to diseases such as cancer and inflammation.

DBU Phenolate can form a covalent bond with the active site serine residue of serine proteases, effectively inhibiting their activity. This inhibition is irreversible, meaning that once the enzyme is inactivated, it cannot be reactivated. This property makes DBU Phenolate a valuable tool for studying the kinetics and mechanisms of serine protease action.

Example: Trypsin Inhibition

Trypsin is a well-known serine protease that cleaves proteins at the carboxyl side of lysine and arginine residues. In a study by Smith et al. (2010), DBU Phenolate was used to inhibit trypsin activity in vitro. The researchers found that DBU Phenolate formed a stable complex with trypsin, leading to a significant reduction in enzyme activity. Moreover, the inhibition was concentration-dependent, with higher concentrations of DBU Phenolate resulting in more pronounced inhibition.

2. Drug Discovery

The development of new drugs is a complex and time-consuming process that requires the identification of molecules that can selectively target disease-causing proteins. DBU Phenolate has shown promise as a lead compound in the discovery of novel therapeutics, particularly for diseases involving protein misfolding and aggregation.

Protein Misfolding and Aggregation

Protein misfolding and aggregation are hallmarks of many neurodegenerative diseases, including Alzheimer’s, Parkinson’s, and Huntington’s disease. These diseases are characterized by the accumulation of abnormal protein aggregates in the brain, which disrupt normal cellular function and lead to neuronal death.

DBU Phenolate has been shown to inhibit the formation of protein aggregates by stabilizing the native conformation of proteins. In a study by Zhang et al. (2015), DBU Phenolate was tested for its ability to prevent the aggregation of amyloid-beta peptides, which are implicated in Alzheimer’s disease. The results showed that DBU Phenolate significantly reduced the formation of amyloid-beta fibrils, suggesting its potential as a therapeutic agent for Alzheimer’s disease.

Example: Huntington’s Disease

Huntington’s disease is caused by the expansion of a polyglutamine repeat in the huntingtin protein, leading to the formation of toxic protein aggregates. In a study by Lee et al. (2018), DBU Phenolate was used to treat cells expressing mutant huntingtin protein. The researchers found that DBU Phenolate reduced the levels of aggregated huntingtin and improved cell viability. These findings suggest that DBU Phenolate could be a promising candidate for the treatment of Huntington’s disease.

3. Nucleic Acid Chemistry

Nucleic acids, such as DNA and RNA, are essential components of all living organisms. They carry genetic information and play a critical role in gene expression and regulation. DBU Phenolate has several applications in nucleic acid chemistry, particularly in the synthesis and modification of oligonucleotides.

Phosphoramidite Coupling

One of the most common methods for synthesizing oligonucleotides is the phosphoramidite method. This technique involves the stepwise coupling of nucleotide building blocks to form a growing DNA or RNA chain. DBU Phenolate has been used as a base catalyst in phosphoramidite coupling reactions, improving the efficiency and yield of the synthesis.

In a study by Brown et al. (2012), DBU Phenolate was compared to other bases, such as tetrazole and imidazole, in phosphoramidite coupling reactions. The results showed that DBU Phenolate provided superior coupling efficiency, with fewer side products and higher overall yields. This improvement is attributed to the high basicity and nucleophilicity of DBU Phenolate, which promotes the deprotonation of the 5′-hydroxyl group of the growing oligonucleotide.

Example: RNA Synthesis

RNA is a single-stranded nucleic acid that plays a variety of roles in the cell, including messenger RNA (mRNA), transfer RNA (tRNA), and ribosomal RNA (rRNA). The synthesis of RNA oligonucleotides is important for studying RNA structure and function, as well as for developing RNA-based therapies.

In a study by Wang et al. (2016), DBU Phenolate was used to synthesize RNA oligonucleotides using the phosphoramidite method. The researchers found that DBU Phenolate improved the coupling efficiency of RNA monomers, particularly for difficult-to-couple bases such as guanosine. This result suggests that DBU Phenolate could be a valuable tool for the large-scale synthesis of RNA oligonucleotides.

4. Analytical Chemistry

Analytical chemistry is the branch of chemistry that deals with the identification and quantification of chemical substances. DBU Phenolate has several applications in analytical chemistry, particularly in the analysis of small molecules and biomolecules.

Fluorescence Quenching

Fluorescence quenching is a technique used to detect and quantify the interaction between molecules. When a fluorescent molecule is brought into close proximity with a quencher, the fluorescence signal is reduced. DBU Phenolate has been used as a quencher in fluorescence-based assays due to its ability to interact with aromatic compounds.

In a study by Kim et al. (2014), DBU Phenolate was used to quench the fluorescence of a fluorophore-labeled peptide. The researchers found that DBU Phenolate efficiently quenched the fluorescence signal, with a quenching efficiency of over 90%. This result suggests that DBU Phenolate could be used as a quencher in fluorescence-based biosensors and imaging applications.

Example: Drug Screening

Drug screening is a critical step in the drug discovery process, where large libraries of compounds are tested for their ability to modulate the activity of a target protein. Fluorescence-based assays are commonly used in high-throughput drug screening due to their sensitivity and ease of use.

In a study by Li et al. (2017), DBU Phenolate was used as a quencher in a fluorescence-based assay to screen for inhibitors of a kinase enzyme. The researchers found that DBU Phenolate effectively quenched the fluorescence signal of a substrate-bound fluorophore, allowing for the detection of enzyme inhibitors. This approach could be applied to the screening of other enzymes and targets, making DBU Phenolate a valuable tool in drug discovery.

5. Environmental Science

Environmental science is the study of the natural environment and the impact of human activities on it. DBU Phenolate has found applications in environmental science, particularly in the analysis of pollutants and the development of green chemistry techniques.

Pollutant Degradation

Pollutants such as pesticides, industrial chemicals, and pharmaceuticals can persist in the environment for long periods, posing a threat to ecosystems and human health. DBU Phenolate has been investigated for its ability to degrade certain types of pollutants through catalytic oxidation.

In a study by Chen et al. (2019), DBU Phenolate was used to catalyze the degradation of chlorinated organic compounds, such as polychlorinated biphenyls (PCBs). The researchers found that DBU Phenolate promoted the oxidation of PCBs in the presence of hydrogen peroxide, leading to the formation of less toxic products. This result suggests that DBU Phenolate could be used in environmental remediation efforts to reduce the levels of persistent organic pollutants.

Example: Water Treatment

Water treatment is a critical process for removing contaminants from drinking water and wastewater. Traditional water treatment methods, such as chlorination and ozonation, can produce harmful byproducts. DBU Phenolate has been explored as a green alternative for water treatment due to its ability to catalyze the degradation of organic pollutants without generating harmful byproducts.

In a study by Liu et al. (2020), DBU Phenolate was used to treat water contaminated with organic dyes. The researchers found that DBU Phenolate efficiently degraded the dyes through catalytic oxidation, with no detectable byproducts. This result suggests that DBU Phenolate could be a valuable tool for the development of environmentally friendly water treatment technologies.

Conclusion

In conclusion, DBU Phenolate (CAS 57671-19-9) is a versatile and powerful compound with a wide range of applications in biochemical research. From enzyme catalysis to drug discovery, nucleic acid chemistry, analytical chemistry, and environmental science, DBU Phenolate has proven to be an invaluable tool for researchers in various fields. Its unique properties, including high basicity, nucleophilicity, and stability, make it an attractive choice for a variety of experiments and applications.

As we continue to explore the potential of DBU Phenolate, we can expect to see even more innovative uses of this compound in the future. Whether you’re a seasoned biochemist or a curious newcomer, DBU Phenolate is definitely a compound worth keeping in your toolkit. So, why not give it a try? You might just discover something amazing!

References

  • Smith, J., et al. (2010). "Mechanism-Based Inhibition of Trypsin by DBU Phenolate." Journal of Biological Chemistry, 285(45), 34678-34685.
  • Zhang, L., et al. (2015). "Inhibition of Amyloid-Beta Fibril Formation by DBU Phenolate." Biochemistry, 54(12), 2015-2022.
  • Lee, H., et al. (2018). "DBU Phenolate Reduces Huntingtin Aggregation and Improves Cell Viability." Nature Communications, 9(1), 1234.
  • Brown, T., et al. (2012). "Improved Phosphoramidite Coupling Efficiency Using DBU Phenolate." Nucleic Acids Research, 40(18), 8877-8884.
  • Wang, X., et al. (2016). "Synthesis of RNA Oligonucleotides Using DBU Phenolate as a Base Catalyst." Chemistry & Biology, 23(5), 567-574.
  • Kim, Y., et al. (2014). "Fluorescence Quenching by DBU Phenolate for Biosensor Applications." Analytical Chemistry, 86(10), 5123-5129.
  • Li, Z., et al. (2017). "High-Throughput Screening of Kinase Inhibitors Using DBU Phenolate as a Fluorescence Quencher." ACS Chemical Biology, 12(6), 1567-1573.
  • Chen, R., et al. (2019). "Catalytic Oxidation of Polychlorinated Biphenyls by DBU Phenolate." Environmental Science & Technology, 53(12), 7215-7222.
  • Liu, M., et al. (2020). "Degradation of Organic Dyes in Water Using DBU Phenolate." Water Research, 179, 115867.

Extended reading:https://www.bdmaee.net/neodecanoic-acid-zinc-cas27253-29-8-zinc-neodecanoate/

Extended reading:https://www.bdmaee.net/butyltinhydroxide-oxide/

Extended reading:https://www.morpholine.org/polyurethane-catalyst-dabco-dc2-strong-gel-catalyst-dabco-dc2/

Extended reading:https://www.bdmaee.net/toyocat-rx5-catalyst-trimethylhydroxyethyl-ethylenediamine-tosoh/

Extended reading:https://www.newtopchem.com/archives/171

Extended reading:https://www.bdmaee.net/dabco-pt305-reactive-amine-catalyst-pt305-dabco-amine-catalyst/

Extended reading:https://www.bdmaee.net/u-cat-651m-catalyst-cas112-99-5-sanyo-japan/

Extended reading:https://www.newtopchem.com/archives/44276

Extended reading:https://www.cyclohexylamine.net/polyurethane-gel-type-catalyst-dabco-low-odor-catalyst/

Extended reading:https://www.bdmaee.net/nt-cat-t12-catalyst-cas280-57-9-newtopchem/

1•595596597598599•2238
Page 597 of 2238