6226-25-1 | 2,2,2-Trifluoroethyl trifluoromethanesulfonate

CAS:6226-25-1 | 2,2,2-Trifluoroethyl trifluoromethanesulfonate ,Description

2,2,2-Trifluoroethyl trifluoromethanesulfonate (TFMS) is an organic compound that has been widely used as a reagent in a variety of chemical and biochemical processes. It is a versatile reagent that can be used in both in vitro and in vivo applications. TFMS is an important compound in many research and industrial applications due to its unique properties.
 

Scientific Research Applications

Catalyst in Organic Synthesis

2,2,2-Trifluoroethyl trifluoromethanesulfonate is utilized in organic synthesis, particularly as a catalyst. It demonstrates significant activity in acylation processes, such as the acylation of alcohols with acid anhydrides or esterification of alcohols by carboxylic acids, notably in the presence of p-nitrobenzoic anhydrides. Its high catalytic efficiency is effective for primary alcohols and even sterically-hindered secondary or tertiary alcohols, making it a valuable tool in selective macrolactonization of omega-hydroxy carboxylic acids (Ishihara, Kubota, Kurihara, & Yamamoto, 1996).

In Cyclization Reactions

This compound is a useful catalyst in inducing cyclization reactions. For example, trifluoromethanesulfonic (triflic) acid catalyzes the 5-endo cyclization of homoallylic sulfonamides to pyrrolidines, showing preference for certain reaction pathways in competitive experiments and making it viable for the formation of polycyclic systems (Haskins & Knight, 2002).

In Cross-Coupling Reactions

Vinyl and aryl trifluoromethanesulfonates, including 2,2,2-Trifluoroethyl trifluoromethanesulfonate, have been increasingly used due to their ease of preparation and versatile reactivity. They undergo cross-coupling reactions with organo-metallics similar to organic halides, addition reactions to alkenes and alkynes, and are particularly effective in Heck reactions. Additionally, these compounds are employed in palladium-catalyzed carbon monoxide insertion and deoxygenation procedures (Ritter, 1993).

Synthesis and Reaction Analysis

The compound is actively used in synthesizing and analyzing various chemical reactions. For instance, in the synthesis of (2,2,2-Trifluoroethyl)triphenylphosphonium Trifluoromethanesulfonate, it facilitates reactions with aromatic aldehydes and secondary amines, leading to the formation of diverse chemical structures (Hanamoto, Morita, & Shindo, 2003).

Ionic Liquids and Force Field Modeling

It plays a role in the creation of ionic liquids, specifically in the study and comparison of various anions. This includes examining the properties like mass density and dynamic viscosity of ionic liquids containing anions combined with commonly used cations. These studies are crucial in validating re-parameterizations of force fields for molecular dynamics simulations of ionic liquids (Gouveia et al., 2017).

More Information