421-85-2 | Trifluoromethanesulfonamide

CAS:421-85-2 | Trifluoromethanesulfonamide ,Description

Trifluoromethanesulfonamide (TFMS) is a versatile molecule that is used in a variety of scientific research applications. It is a crystalline, white solid with a melting point of around 100 °C and a boiling point of around 140 °C. It has a molecular formula of C2H3F3NO2S and is a member of the sulfonamide family. TFMS is a highly reactive compound, and is an important reagent in organic synthesis. It is also a key intermediate in the production of pharmaceuticals and other chemicals. 
 

Scientific Research Applications

Catalytic Applications

Trifluoromethanesulfonic acid, a derivative of trifluoromethanesulfonamide, is an excellent catalyst for cyclisation reactions, particularly in the formation of pyrrolidines and homopiperidines from homoallylic sulfonamides. Its efficiency in catalyzing the formation of polycyclic systems has been noted in research (Haskins & Knight, 2002).

Synthesis and Applications

Trifluoromethanesulfonamide, also known as triflamide, finds wide application in organic reactions due to its unique properties like high NH-acidity and strong electron-withdrawing nature. It plays a significant role in various organic reactions, including cycloaddition, Friedel–Crafts reactions, and C-amination, contributing to the synthesis of valuable compounds in organic chemistry, medicine, and agriculture (Moskalik & Astakhova, 2022).

Lewis Acid Catalysis

Scandium trifluoromethanesulfonate, another derivative, is recognized for its remarkably high catalytic activity, especially in the acylation of alcohols with acid anhydrides and esterification processes. This catalyst is particularly effective in selective macrolactonization of omega-hydroxy carboxylic acids, demonstrating its potential in various organic synthesis applications (Ishihara, Kubota, Kurihara, & Yamamoto, 1996).

Spectroscopic Study

Trifluoromethanesulfonamide has been studied using infrared and Raman techniques. These studies, supported by ab initio calculations, help in understanding the molecular structure and vibrational modes, which are crucial for its application in various chemical processes (Fernández, Altabef, Fantoni, & Varetti, 1997) .

Vinyl and Aryl Triflates Synthesis

Vinyl and aryl trifluoromethanesulfonates, derived from trifluoromethanesulfonamide, are used extensively due to their ease of preparation and application in cross-coupling reactions. These compounds are superior in regio- and diastereoselectivity compared to halides, highlighting their importance in natural product synthesis and various deoxygenation procedures (Ritter, 1993).

Formation and Structure of Heterocycles

Trifluoromethanesulfonamide is also essential in forming heterocycles through condensation with carbonyl compounds. Its high NH-acidity makes it an interesting subject for studying the structure and stereodynamic behavior of the resulting heterocycles, which have implications in synthetic organic chemistry (Shainyan & Meshcheryakov, 2009).

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