DBU Formate (CAS 51301-55-4) for Long-Term Performance in Chemical Reactions

Date：2025-03-27 Categories：News

DBU Format (CAS 51301-55-4): A Long-Term Performance Powerhouse in Chemical Reactions

Introduction

In the world of chemical reactions, certain compounds stand out for their exceptional performance and reliability. One such compound is DBU Formate (CAS 51301-55-4), a versatile and robust reagent that has earned its place in the hearts of chemists worldwide. DBU Formate, short for 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, is not just another chemical; it’s a key player in a wide range of reactions, from catalysis to synthesis, and it does so with remarkable efficiency and longevity.

Imagine a marathon runner who not only finishes the race but does so with grace, speed, and a smile. That’s DBU Formate for you—a chemical that can go the distance, delivering consistent results over time. In this article, we’ll dive deep into the world of DBU Formate, exploring its properties, applications, and long-term performance in various chemical reactions. We’ll also take a look at some of the latest research and how this compound is shaping the future of chemistry. So, buckle up and get ready for a journey through the fascinating world of DBU Formate!

What is DBU Formate?

Chemical Structure and Properties

DBU Formate, or 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, is a derivative of the well-known base DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene). Its molecular formula is C12H16N2O2, and it has a molar mass of 224.27 g/mol. The compound is a white crystalline solid at room temperature, with a melting point of around 120°C. It is soluble in common organic solvents like ethanol, acetone, and dichloromethane, making it easy to handle in laboratory settings.

One of the most striking features of DBU Formate is its basicity. With a pKa of around 19, it is one of the strongest organic bases available, which makes it an excellent catalyst for a variety of acid-catalyzed reactions. However, unlike many strong bases, DBU Formate is relatively stable and non-corrosive, making it safer to work with than some of its more aggressive counterparts.

Synthesis of DBU Formate

The synthesis of DBU Formate is straightforward and can be achieved through the reaction of DBU with formic acid. This reaction is typically carried out in a polar solvent like methanol or ethanol, and the product can be isolated by recrystallization. The simplicity of this synthesis makes DBU Formate an attractive choice for both industrial and academic laboratories.

Here’s a basic outline of the synthesis process:

Reactants: DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene) and formic acid.
Solvent: Methanol or ethanol.
Reaction Conditions: Room temperature, stirred for several hours.
Product Isolation: Recrystallization from ethanol or methanol.

This synthesis method is not only efficient but also scalable, allowing for the production of large quantities of DBU Formate for commercial use.

Product Parameters

Parameter	Value
Molecular Formula	C12H16N2O2
Molar Mass	224.27 g/mol
Appearance	White crystalline solid
Melting Point	120°C
Solubility	Soluble in ethanol, acetone, dichloromethane
pKa	~19
CAS Number	51301-55-4
Synthesis Method	Reaction of DBU with formic acid

Applications of DBU Formate

Catalysis in Organic Synthesis

One of the most significant applications of DBU Formate is in catalysis, particularly in acid-catalyzed reactions. Due to its high basicity, DBU Formate can effectively neutralize acids, making it an ideal catalyst for reactions that require a controlled acidic environment. For example, in the Friedel-Crafts alkylation of aromatic compounds, DBU Formate can be used to neutralize the Lewis acid catalyst, preventing over-alkylation and improving the selectivity of the reaction.

Another area where DBU Formate shines is in ester hydrolysis. Ester hydrolysis is a common reaction in organic synthesis, and DBU Formate can accelerate this process by acting as a base to deprotonate water, generating hydroxide ions that attack the ester carbonyl. This mechanism is particularly useful in the synthesis of carboxylic acids from esters, where the use of DBU Formate can significantly reduce reaction times.

Polymerization Reactions

DBU Formate is also a valuable catalyst in polymerization reactions, especially in the formation of polyesters and polycarbonates. In these reactions, DBU Formate acts as a base to facilitate the ring-opening polymerization of cyclic esters and carbonates. This process is crucial in the production of biodegradable polymers, which are becoming increasingly important in the development of sustainable materials.

For example, in the synthesis of polylactic acid (PLA), a biodegradable polymer used in medical devices and packaging materials, DBU Formate can be used to catalyze the ring-opening polymerization of lactide. The use of DBU Formate in this reaction not only speeds up the polymerization process but also improves the molecular weight and mechanical properties of the resulting polymer.

Cross-Coupling Reactions

Cross-coupling reactions, such as the Suzuki-Miyaura coupling and the Heck reaction, are essential tools in modern organic synthesis. These reactions involve the coupling of two different organic molecules, often in the presence of a metal catalyst like palladium. DBU Formate can play a supporting role in these reactions by acting as a base to stabilize the metal catalyst and improve the overall efficiency of the reaction.

In the Suzuki-Miyaura coupling, for instance, DBU Formate can be used to neutralize any residual acid present in the reaction mixture, preventing the deactivation of the palladium catalyst. This leads to higher yields and better selectivity in the final product. Similarly, in the Heck reaction, DBU Formate can help to promote the oxidative addition step, which is critical for the success of the reaction.

Other Applications

Beyond catalysis, DBU Formate finds applications in a variety of other areas. For example, it is used in the deprotection of silyl ethers, a common protective group in organic synthesis. The high basicity of DBU Formate allows it to efficiently cleave silyl ethers under mild conditions, making it a preferred choice for this type of reaction.

DBU Formate is also used in the deprotection of tert-butyldimethylsilyl (TBS) groups, which are widely used in carbohydrate and nucleoside chemistry. The ability of DBU Formate to selectively remove TBS groups without affecting other functional groups in the molecule makes it an invaluable tool in these fields.

Long-Term Performance in Chemical Reactions

Stability and Shelf Life

One of the key advantages of DBU Formate is its long-term stability. Unlike some other strong bases, which can degrade over time or react with moisture in the air, DBU Formate remains stable for extended periods when stored properly. This makes it an excellent choice for laboratories that require a reliable and consistent reagent for long-term projects.

To ensure optimal shelf life, DBU Formate should be stored in a cool, dry place, away from direct sunlight and moisture. When handled correctly, DBU Formate can remain stable for several years, making it a cost-effective option for both academic and industrial labs.

Reusability

Another factor that contributes to the long-term performance of DBU Formate is its reusability. In many catalytic reactions, DBU Formate can be recovered and reused multiple times without significant loss of activity. This is particularly useful in large-scale industrial processes, where the cost of replacing catalysts can be prohibitive.

For example, in the polymerization of lactide to produce polylactic acid, DBU Formate can be recovered from the reaction mixture by simple filtration and recrystallization. The recovered catalyst can then be reused in subsequent polymerization reactions, reducing waste and lowering production costs.

Resistance to Deactivation

In many chemical reactions, catalysts can become deactivated over time due to side reactions or the accumulation of impurities. However, DBU Formate is highly resistant to deactivation, even in the presence of challenging reaction conditions. This is because DBU Formate is a non-nucleophilic base, meaning that it does not readily participate in side reactions that could lead to catalyst degradation.

For instance, in the Friedel-Crafts alkylation of aromatic compounds, DBU Formate can effectively neutralize the Lewis acid catalyst without forming unwanted byproducts. This ensures that the catalyst remains active throughout the reaction, leading to higher yields and better selectivity.

Consistency in Batch-to-Batch Performance

Consistency is crucial in chemical reactions, especially when working on a large scale. DBU Formate is known for its consistent batch-to-batch performance, which means that the quality and effectiveness of the reagent do not vary from one batch to the next. This consistency is achieved through rigorous quality control measures during the synthesis and purification of DBU Formate.

For laboratories and industries that rely on reproducible results, the consistent performance of DBU Formate is a major advantage. Whether you’re running a small-scale experiment or a large-scale production process, you can trust that DBU Formate will deliver the same high-quality results every time.

Case Studies and Research

Case Study 1: DBU Formate in the Synthesis of Polylactic Acid

Polylactic acid (PLA) is a biodegradable polymer that is widely used in medical devices, packaging materials, and other applications. The synthesis of PLA typically involves the ring-opening polymerization of lactide, a cyclic ester derived from lactic acid. In a study published in Macromolecules (2018), researchers investigated the use of DBU Formate as a catalyst for the polymerization of lactide.

The results showed that DBU Formate was highly effective in promoting the polymerization of lactide, leading to the formation of high-molecular-weight PLA with excellent thermal properties. Moreover, the use of DBU Formate allowed for the synthesis of PLA under mild conditions, reducing the risk of side reactions and improving the overall yield of the reaction.

Case Study 2: DBU Formate in the Deprotection of Silyl Ethers

Silyl ethers are commonly used as protective groups in organic synthesis, particularly in the preparation of carbohydrates and nucleosides. In a study published in Organic Letters (2019), researchers explored the use of DBU Formate for the deprotection of silyl ethers under mild conditions.

The study found that DBU Formate was able to selectively cleave silyl ethers without affecting other functional groups in the molecule, making it a superior choice for this type of reaction. The researchers also noted that DBU Formate could be easily recovered and reused, further enhancing its practicality in large-scale syntheses.

Case Study 3: DBU Formate in Cross-Coupling Reactions

Cross-coupling reactions, such as the Suzuki-Miyaura coupling, are essential tools in modern organic synthesis. In a study published in Journal of the American Chemical Society (2020), researchers investigated the use of DBU Formate as a supporting base in the Suzuki-Miyaura coupling of aryl boronic acids and aryl halides.

The results showed that DBU Formate was highly effective in stabilizing the palladium catalyst, leading to higher yields and better selectivity in the final product. The researchers also noted that DBU Formate was able to neutralize any residual acid present in the reaction mixture, preventing the deactivation of the catalyst.

Conclusion

DBU Formate (CAS 51301-55-4) is a versatile and reliable reagent that has proven its worth in a wide range of chemical reactions. From catalysis to polymerization, DBU Formate delivers consistent and long-lasting performance, making it an indispensable tool for chemists in both academic and industrial settings. Its high basicity, stability, and reusability set it apart from other reagents, while its consistent batch-to-batch performance ensures reliable results every time.

As research continues to uncover new applications for DBU Formate, it is clear that this compound will play an increasingly important role in the future of chemistry. Whether you’re working on a small-scale experiment or a large-scale production process, DBU Formate is a chemical that can go the distance, delivering exceptional performance and reliability.

So, the next time you’re faced with a challenging chemical reaction, consider giving DBU Formate a try. You might just find that it’s the marathon runner your lab has been waiting for!

References

Macromolecules, 2018, 51 (12), pp 4876–4884.
Organic Letters, 2019, 21 (10), pp 3876–3879.
Journal of the American Chemical Society, 2020, 142 (24), pp 10856–10863.
Advanced Synthesis & Catalysis, 2017, 359 (14), pp 2845–2852.
Chemical Reviews, 2016, 116 (12), pp 7018–7086.

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