433-06-7 | 2,2,2-Trifluoroethyl p-toluenesulfonate

CAS:433-06-7 | 2,2,2-Trifluoroethyl p-toluenesulfonate ,Description

2,2,2-Trifluoroethyl p-toluenesulfonate (TFE-TOS) is an organosulfur compound with the chemical formula C7H5F3OS. It is a colorless solid that is soluble in organic solvents. TFE-TOS is used as a reagent and catalyst in organic synthesis, and has been studied for its potential applications in biochemistry and medicine.
 

Scientific Research Applications

Synthesis of Disubstituted 1,1-Difluoro-1-Alkenes

2,2,2-Trifluoroethyl p-toluenesulfonate plays a pivotal role in the synthesis of disubstituted 1,1-difluoro-1-alkenes. The process involves treating it with lithium diisopropylamide and trialkylboranes, followed by coupling with aryl iodides in the presence of a palladium catalyst and tetrabutylammonium fluoride, resulting in good yields of these alkenes (Ichikawa et al., 1991).

Synthesis of 2,2-Difluorovinyl Carbonyl Compounds

This compound is also essential in synthesizing 2,2-difluorovinyl carbonyl compounds. The process includes treatment with butyllithium and trialkylboranes, and subsequent reaction with acyl chlorides or chloroformates in the presence of cuprous iodide, yielding good amounts of these compounds (Ichikawa et al., 1992).

Preparation of Arylthioynamines

In the preparation of arylthioynamines, 2,2,2-Trifluoroethyl p-toluenesulfonate reacts with sodium thiolates, followed by a reaction with lithium dialkylamides to yield these compounds in good yields (Nakai et al., 1977).

Synthesis of Fluorinated Isochromenes and Isothiochromenes

This compound is instrumental in synthesizing 3-fluorinated isochromenes and 3-fluoroisothiochromenes. It involves the preparation of β,β-difluorostyrenes and their subsequent intramolecular nucleophilic substitution leading to these compounds in high yields (Wada et al., 2001) .

Friedel-Crafts Cyclization

In Friedel-Crafts cyclization, 1,1-difluoroalk-1-enes obtained from 2,2,2-trifluoroethyl p-toluenesulfonate are treated with FSO3H.SbF5, leading to the formation of bicyclic ketones through α-fluorocarbocations (Ichikawa et al., 2004).

Synthesis of gem-Difluoro-penta-1,4-Dienes

The compound aids in synthesizing functionalized gem-difluoro-penta-1,4-dienes, involving a reaction with α-ethoxycarbonyl vinylphosphonate and various aldehydes, yielding these dienes in significant amounts (Shen et al., 2001).

Electrochemical Studies in Non-aqueous Solvents

It is used in studying the polarographic reduction of alkaline earth and transition metal ions in non-aqueous solvents like N,N-dimethylformamide and acetonitrile (Fujinaga & Sakamoto, 1976).

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