Trifluoromethanesulfonic Anhydride

[358-23-6] C2F6O5S2 (MW 282.16) InChI = 1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8 InChIKey = WJKHJLXJJJATHN-UHFFFAOYSA-N (preparation of triflates;1 mild dehydrating reagent; promoter for coupling reactions in carbohydrates2) Alternate Name: triflic anhydride. Physical Data: bp 81–83 °C/745 mmHg; d 1.677 g cm−3; n20D 1.3210. Solubility: soluble in dichloromethane; insoluble in hydrocarbons. Form Supplied in: colorless liquid in ampules. Once opened it should be immediately used. IR, NMR. Preparative Methods: by distillation of Trifluoromethanesulfonic Acid with an excess of Phosphorus(V) sulfide.1 by redistillation with a small amount of P2O5. It is advisable to freshly distill the reagent from a small quantity of P2O5 before use. Handling, Storage, and Precautions: the pure reagent is a colorless liquid that does not fume in air and is stable for a long period. It is not soluble in water and hydrolyzes only very slowly to triflic acid over several days at room temperature. Preferably stored under N2 in a stoppered flask. Dangerously exothermic reactions have been reported when attempting to triflate hindered alcohols.67