Trifluoromethanesulfonic anhydride
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| Identifiers | |||
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| ECHA InfoCard | 100.006.016 | ||
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C2F6O5S2 | |||
| Molar mass | 282.13 g·mol−1 | ||
| Density | 1.6770 g/mL | ||
| Boiling point | 82[1] °C (180 °F; 355 K) | ||
| Hazards | |||
| Safety data sheet (SDS) | Fisher MSDS | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
See also
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Baker, T. J. Tomioka, M.; Goodman, M. (2004). "Preparation and Use of N,N'-Di-BOC-N-Triflylguanidine". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10. - ^ McWilliams, J. C. Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D. "Preparation of n-Butyl 4-Chlorophenyl Sulfide". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10, p. 147. - ^ 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)". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 10, p. 112.