tms trifluoromethane sulfonate cas no

3 min read 22-01-2025

Meta Description: Dive deep into TMS trifluoromethanesulfonate (CAS No. 3570-13-4)! This comprehensive guide explores its properties, uses, safety precautions, synthesis, and applications in various fields, including organic chemistry and material science. Learn about its role as a powerful reagent and understand the importance of safe handling practices.

Introduction:

Trimethylsilyl trifluoromethanesulfonate (TMSOTf, CAS No. 3570-13-4) is a powerful and versatile reagent commonly used in organic chemistry. Its strong Lewis acidity and ability to activate various functional groups make it a key player in numerous synthetic transformations. This article delves into the properties, synthesis, applications, safety concerns, and handling of TMS trifluoromethanesulfonate.

Properties of TMS Trifluoromethanesulfonate

TMSOTf is a colorless to light yellow liquid with a pungent odor. Its key properties include:

CAS Number: 3570-13-4
Molecular Formula: C₃H₉F₃O₃SSi
Molecular Weight: 228.26 g/mol
Density: Approximately 1.3 g/cm³
Boiling Point: Decomposes before boiling
Solubility: Soluble in common organic solvents

Its strong Lewis acidity stems from the trifluoromethanesulfonate (triflate) anion, which is a very weakly coordinating anion. This allows the trimethylsilyl (TMS) cation to readily interact with various substrates.

Synthesis of TMS Trifluoromethanesulfonate

TMSOTf is typically synthesized through the reaction of trimethylsilyl chloride (TMSCl) with triflic acid (TfOH) in the presence of a base, such as triethylamine. The reaction proceeds readily and can be scaled up for larger-scale preparations. The precise synthesis method and conditions may vary depending on the desired purity and scale.

Applications of TMS Trifluoromethanesulfonate in Organic Chemistry

TMSOTf's unique properties have led to its widespread use in various organic reactions, including:

Protection and Deprotection: TMSOTf can be employed for the protection and deprotection of various functional groups, including alcohols, amines, and ketones. Its ability to readily form silyl ethers makes it particularly useful in this area.
C-C Bond Formation: TMSOTf serves as a catalyst or reagent in numerous C-C bond-forming reactions, such as aldol condensations and Friedel-Crafts alkylations. Its Lewis acidity facilitates the formation of reactive intermediates.
Silylation Reactions: TMSOTf is a common reagent for silylation reactions, the introduction of a trimethylsilyl group into a molecule. This can enhance the reactivity or stability of the molecule.
Esterification and Transesterification: TMSOTf catalyzes the formation of esters and facilitates transesterification reactions.

Specific Examples of Applications:

Acetal Formation: TMSOTf effectively catalyzes the formation of acetals from aldehydes and ketones with alcohols.
Glycosylation Reactions: Its Lewis acidity makes it useful in glycosylation reactions for the synthesis of oligosaccharides and glycoconjugates.

Safety Precautions and Handling of TMS Trifluoromethanesulfonate

TMSOTf is a highly reactive and corrosive compound. Appropriate safety precautions must be taken during handling:

Eye Protection: Wear safety goggles or a face shield.
Gloves: Use appropriate chemical-resistant gloves.
Ventilation: Work under a well-ventilated fume hood.
Storage: Store in a cool, dry place away from incompatible materials.
Disposal: Dispose of according to local regulations.

Direct contact with skin or eyes can cause severe irritation or burns. Inhalation of fumes should be avoided. Always consult the Safety Data Sheet (SDS) before handling.

TMS Trifluoromethanesulfonate in Material Science

Beyond organic synthesis, TMSOTf finds applications in material science. Its ability to act as a catalyst or reagent in polymerization reactions makes it relevant in the synthesis of certain polymers and functional materials. Research is ongoing to explore its potential in creating new advanced materials.

Conclusion

TMS trifluoromethanesulfonate (CAS No. 3570-13-4) is a valuable reagent in organic chemistry and material science. Its strong Lewis acidity and versatility make it a powerful tool for a wide range of applications. However, its reactivity necessitates careful handling and adherence to strict safety procedures. Understanding its properties, synthesis, applications, and safety precautions is crucial for anyone working with this important chemical compound. Always refer to the relevant safety data sheets and follow appropriate laboratory safety protocols.