Trifluoromethanesulfonic anhydride

Trifluoromethanesulfonic anhydride
Identifiers
CAS Number	358-23-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	61068;
ECHA InfoCard	100.006.016
PubChem CID	67749;
CompTox Dashboard (EPA)	DTXSID501014629 ;
	InChI InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8 Key: WJKHJLXJJJATHN-UHFFFAOYSA-N;
	SMILES C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F;
Properties
Chemical formula	C2F6O5S2
Molar mass	282.13 g·mol−1
Density	1.6770 g/mL
Boiling point	82 °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). verify (what is ?) 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. Abbreviated Tf₂O, 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

^ 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; 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; Collected Volumes, vol. 10, p. 112.

[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.

[Amico2002-3] 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". Organic Syntheses; Collected Volumes, vol. 10.

[5] 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.

[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)". Organic Syntheses; Collected Volumes, vol. 10, p. 112.

[1]

[2]

[3]

[4]

[5]

[6]

Illustrative uses

See also

References