2,2,2-Trifluoroethyl trifluoromethanesulfonate

A fluorine-containing alkyl alkanesulfonate with cyctotoxity towards cultured leukemia L1210 cells.

2,2,2-Trifluoroethyl trifluoromethanesulfonate is a powerful trifluoroethylating agent which is useful for synthesis of fluorinated amino acids. It is used as a reagent in thenantioselective preparation of cyclic N-aryl hydroxamic acids via phase-transfer catalyzed alkylation of nitrobenzyl bromides to give nirophenylalanines.

Reagent used in thenantioselective preparation of cyclic N-aryl hydroxamic acids via phase-transfer catalyzed alkylation of nitrobenzyl bromides to give nirophenylalanines

In a 100-ml flask equipped with a stirrer, a thermometer, a nitrogen introducing pipe, and a condenser, 50 ml (0.297 mol) of trifluoromethane sulfonic anhydride and 25 ml (0.342 moles) of 2,2,2-trifluoroethanol were placed at room temperature and stirred for 30 minutes in a nitrogen atmosphere, followed by reflux for 3 hours. After distillation, 50.3 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate was obtained in a yield of 73%.