Trifluoromethanesulfonic anhydride

This compound is a strong electrophile, useful for introducing the triflyl group, CF3SO2.

[2] Triflic anhydride is useful for converting ketones into enol triflates.

[4] In a representative application, is used to convert an imine into a NTf group.

[5] It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.

Samples of triflic anhydride can be assayed by 19F NMR spectroscopy: −72.6 ppm[8] vs. −77.3 for TfOH (std CFCl3).

Skeletal formula of triflic anhydride
Skeletal formula of triflic anhydride
NFPA 704 four-colored diamond Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas Flammability 0: Will not burn. E.g. water Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide Special hazard W+OX: Reacts with water in an unusual or dangerous manner AND is oxidizer