Trifluoromethanesulfonic anhydride

Trifluoromethanesulfonic anhydride

Skeletal formula of triflic anhydride
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Identifiers
CAS Number	358-23-6 N
PubChem	67749
Properties
Chemical formula	C2F6O5S2
Molar mass	282.13 g·mol−1
Density	1.6770 g/mL
Boiling point	82 °C (180 °F; 355 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.