88284-48-4 | 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate

CAS:88284-48-4 | 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate ,Description

2-(Trimethylsilyl)phenyl trifluoromethanesulfonate, also known as TMS-PTS, is an organosulfur compound that is used as a reagent in organic synthesis. It is a colorless liquid that is soluble in polar solvents such as methanol and ethanol. It is used in a variety of applications, including the synthesis of pharmaceuticals, pesticides, and other organic compounds. TMS-PTS is also used in the preparation of polymers and catalysts.
 

Scientific Research Applications

Applications in Organic Synthesis

The use of trifluoromethanesulfonic acid derivatives, such as 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate, in organic synthesis is well-documented. These compounds play a crucial role in electrophilic aromatic substitution reactions, formation of carbon–carbon, and carbon–heteroatom bonds. Due to their high protonating power and low nucleophilicity, trifluoromethanesulfonic acid derivatives enable the generation of cationic species from organic molecules. These species can be detected and studied using spectral methods, making these derivatives convenient reagents for synthesizing new organic compounds (Kazakova & Vasilyev, 2017).

Peptide Synthesis

In peptide chemistry, acidic deprotecting systems utilizing trifluoromethanesulfonic acid and its derivatives have been employed for removing protecting groups. However, these reagents are not always applicable to peptides containing cystine- or phosphoamino acids. Research has developed efficient and practical reagent systems, including 1 M trimethylsilyl trifluoromethanesulfonate (TMSOTf)-sulfide in trifluoroacetic acid (TFA), suitable for peptide synthesis. These systems allow for the practical synthesis of cystine peptides and phosphopeptides, demonstrating the versatility of trifluoromethanesulfonic acid derivatives in peptide deprotection and synthesis (Otaka, 2000).

Environmental Applications

The degradation and environmental fate of polyfluoroalkyl chemicals, which may involve compounds like 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate, are significant areas of research. Studies focus on the microbial degradation of these chemicals in the environment and their transformation into perfluoroalkyl carboxylic and sulfonic acids. Understanding the biodegradation pathways and half-lives of these precursors is crucial for evaluating their environmental impact and for the development of strategies to mitigate their persistence (Liu & Avendaño, 2013).

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