Trifluoromethanesulfonic anhydride

Trifluoromethanesulfonic anhydride
Identifiers
358-23-6 
Properties
Molecular formula
 C2F6O5S2
Molar mass 282.14 g·mol−1
Density 1.6770 g/mL
Boiling point 82[1] °C (180 °F; 355 K)
Hazards
MSDS Fisher MSDS
R-phrases R14 R34
S-phrases S25 S26 S36/37/39 S45
Except where noted otherwise, data is 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.[2]

It can be assayed by 19F NMR spectroscopy: −72.6 ppm[3] vs. -77.3 for TfOH (std CFCl3).

Illustrative uses

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

It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.[5][6]

References

  1. ↑ Bloodworth, A.J.; Curtis, Richard J.; Spencer, Michael D.; Tallant, Neil A. (March 1993). "Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides.". Tetrahedron 49 (13): 2729–2750. doi:10.1016/S0040-4020(01)86350-X.
  2. ↑ Baraznenok, Ivan L.; Nenajdenko, Valentine G.; Balenkova, Elizabeth S. (May 2000). "Chemical Transformations Induced by Triflic Anhydride". Tetrahedron 56 (20): 3077–3119. doi:10.1016/S0040-4020(00)00093-4.
  3. ↑ Dell'Amico, Daniela Belli; Boschi, Daniele; Calderazzo, Fausto; Labella, Luca; Marchetti, Fabio (28 February 2002). "Synthesis, and crystal and molecular structures of the triflato and trifluoroacetato complexes of zinc, Zn(O3SCF3)2(DME)2 and [Zn(O2CCF3)2(DME)]n" (PDF). Inorganica Chimica Acta 330 (1): 149–154. doi:10.1016/S0020-1693(01)00739-3.
  4. ↑ Baker, T. J. Tomioka, M.; Goodman, M. (2004). "Preparation and Use of N,N'-Di-BOC-N-Triflylguanidine". Org. Synth.; Coll. Vol. 10
  5. ↑ McWilliams, J. C. Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D. "Preparation of n-Butyl 4-Chlorophenyl Sulfide". Org. Synth.; Coll. Vol. 10, p. 147
  6. ↑ Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Org. Synth.; Coll. Vol. 10, p. 112