333-27-7 | Methyl trifluoromethanesulfonate

CAS:333-27-7 | Methyl trifluoromethanesulfonate ,Description

Methyl trifluoromethanesulfonate (MTFMS) is an organic compound with the molecular formula C3H3F3O3S. It is a colorless, odorless, and water-soluble liquid. It has a wide range of applications in scientific research, including as a reagent in organic chemistry, as a catalyst in polymer synthesis, and as a solvent in biological assays. In addition, MTFMS is used in the synthesis of pharmaceuticals, agrochemicals, and other industrial chemicals.
 

Scientific Research Applications

Gas Phase Structure Analysis

Methyl trifluoromethanesulfonate (CH3OSO2CF3) has been studied for its molecular structure using gas electron diffraction and quantum chemical calculations. This research provides insights into the conformational properties of covalent sulfonates, revealing a gauche conformation with specific dihedral angles and bond lengths, contributing to a deeper understanding of its molecular behavior (Trautner et al., 1999).

Catalyst in Acylation Reactions

Scandium trifluoromethanesulfonate, closely related to methyl trifluoromethanesulfonate, serves as an effective Lewis acid catalyst for acylation of alcohols with acid anhydrides and for esterification of alcohols. This catalyst facilitates acylation even in sterically-hindered alcohols and is particularly efficient in selective macrolactonization of omega-hydroxy carboxylic acids (Ishihara et al., 1996).

Synthesis of Radioactive Tracers

Methyl trifluoromethanesulfonate has been used in the synthesis of [11C]methyl triflate, a compound relevant in the field of radiotracer chemistry. This synthesis involves the conversion of [11C]methyl iodide into [11C]methyl triflate, demonstrating its utility in producing compounds for medical imaging (Jewett, 1992).

Trifluoromethanesulfonic Acid in Organic Synthesis

While not directly methyl trifluoromethanesulfonate, trifluoromethanesulfonic acid (a related compound) has a significant role in organic synthesis. Its high protonating power and low nucleophilicity enable the generation of cationic species from organic molecules, aiding in various reactions including electrophilic aromatic substitution and the formation of carbon-heteroatom bonds (Kazakova & Vasilyev, 2017).

Electrophilic Reactions in Organic Chemistry

The study of N-hydroxymethylphthalimide in trifluoromethanesulfonic acid (triflic acid) showcases its reactivity with various aromatic compounds, producing α-amidomethylated products. This highlights its application in extending the scope of α-amido-methylation reactions in organic chemistry (Olah et al., 1993).

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