Puneet Varma (Editor)

Trifluoromethanesulfonic anhydride

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Density
  
1.68 g/cm³

Chemical formula
  
C2F6O5S2

Pubchem
  
67749

Molar mass
  
282.13 g·mol−1

R-phrases
  
R14 R34

Boiling point
  
82 °C (180 °F; 355 K)

Trifluoromethanesulfonic anhydride httpsuploadwikimediaorgwikipediacommonsthu

Triflic anhydride is the chemical compound with the formula (CF3SO2)2O. This compound is a particularly strong electrophile, useful for introducing the triflyl group, CF3SO2. Triflic anhydride is the acid anhydride of the strong acid triflic acid, CF3SO2OH.

It can be assayed by 19F NMR spectroscopy: −72.6 ppm vs. -77.3 for TfOH (std CFCl3).

Illustrative uses

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

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

References

Trifluoromethanesulfonic anhydride Wikipedia