Trifluoromethanesulfonic acid, also known as triflic acid, TFMS, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest acids. Triflic acid is a hygroscopic, colorless liquid at room temperature. . It is soluble in polar solvents. Its melting point is -40 C and boiling point is 162°C. It’s miscible in water. When contacted with moist in air, it forms a hydrated solid. . Unlike sulfuric acid, fluorosulfuric acid or chlorosulfuric acid, it does not lead to sulfonations and can be used in various protonation reactions. This novel collection of properties has made triflic acid an important reagent and catalyst in modern synthetic chemistry. As a comparatively new substance –it was first reported in 1954 and subsequently commercialized– researchers continue to find new and interesting applications of triflic acid.
Uses and Applications
Triflic acid, its salts, acid halides, anhydrides and esters are used as a catalyst for the reactions of: condensation of alcohols and carboxylic acids, reaction of aromatic compounds with sulfonyl chlorides, cracking of alkanes, alkylation of alkenes, isomerisation of alkanes, trans-alkylation of aromatics a trans-bromination and other Friedel-Crafts reactions.Triflic acid is a convenient and non hazardous acid for the Thiele-Winter reaction of quinones. The synthetic scope of the Thiele-Winter reaction was increased by the use of triflic acid. Because of the hygroscopic nature of triflic acid, handling and transfer under a dry, inert atmosphere is recommended.More than twenty metal salts of triflic acid have been reported in the literature. Their use as catalysts and reagents is an important and growing area of modern synthetic chemistry, particularly in fine chemical synthesis.It is used as a catalyst in the manufacture of pharmaceuticals, agricultural chemicals and polymers, while the anhydride form is used in fine chemical synthesis.
Super acid-catalyzed reactions and ionic reagents (obtained under superacidic,
stable ion conditions) are gaining increasing significance in synthetic and natural
product chemistry and this trend is expected to continue and expand. Future development of new and improved superacidic systems, particularly allowing long on stream time in catalytic applications without deactivation and ease of regeneration, is of particular interest. Applications of superacids are foreseen to expand in catalysis and in synthetic chemistry, as well as in preparation and study of reactive ionic intermediates. It is rewarding to see that many of our expectations have materialized during the last two decades. The use of superacids has become common practice in synthetic organic chemistry as demonstrated by the numerous new areas of applications, including particularly their use in the chemistry of hydrocarbons, protecting groups, heterocycles, and carbohydrates. Furthermore, superacids have also found wide application in the generation of varied inorganic cations and complexes.