1493-13-6 | Trifluoromethanesulfonic acid

CAS:1493-13-6 | Trifluoromethanesulfonic acid ,Description

Trifluoromethanesulfonic acid (TFMSA), also known as trifluoromethanesulphonic acid or trifluoromethanesulfonic anhydride, is a powerful and versatile acid. It is a colorless and odorless liquid, and is a powerful fluorinating and oxidizing agent. TFMSA is a strong acid, with a pKa of -1.7, and is used in a variety of applications, such as in organic synthesis, as a catalyst in chemical reactions, and in the production of pharmaceuticals and other compounds.
 

Scientific Research Applications

• Catalytic Applications:
  • Trifluoromethanesulfonic acid is a highly effective catalyst in acylation reactions. It's particularly potent for acylating not only primary alcohols but also sterically-hindered secondary or tertiary alcohols, useful in macrolactonization of omega-hydroxy carboxylic acids (Ishihara et al., 1996).
  • It is one of the superior catalysts for C- and/or O-acylation, with broad applicability under mild and neat conditions. Its unique controllability in catalytic activity is notable (Tachrim et al., 2017).
• Organic Synthesis:
  • In organic synthesis, trifluoromethanesulfonic acid assists in electrophilic aromatic substitution reactions, formation of carbon–carbon and carbon–heteroatom bonds, isomerizations, syntheses of carbo and heterocyclic structures, and more. Its high protonating power and low nucleophilicity enable the generation of cationic species from organic molecules for spectral detection and study (Kazakova & Vasilyev, 2017).
• Electrochemical Applications:
  • Trifluoromethanesulfonic acid is used in cyclic voltammetry as a solvent, facilitating electrochemistry up to +3 V. Its use as an electrolyte in fuel cell systems is due to the enhanced rate of oxygen reduction (Bernhard et al., 1990).
• Fuel Cell Applications:
  • It resembles Nafion® in structure and has applications in direct alcohol fuel cells, demonstrated in the formation of membranes by the fixation of erbium triflate salts into the Nafion structure (Barbora et al., 2009).
• Polymer Science:
  • Employed as a catalyst for the cyclization of polyisoprene, trifluoromethanesulfonic acid has shown higher efficiency compared to other strong acids like methanesulfonic acid (Chan & Lin, 2006).

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