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Trifluoromethanesulfonic anhydride
Names
	Preferred IUPAC name Trifluoromethanesulfonic anhydride
Identifiers
CAS Number	358-23-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48509;
ChemSpider	61068;
ECHA InfoCard	100.006.016
EC Number	206-616-8;
PubChem CID	67749;
UNII	8W034LHG1U ;
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
Appearance	colourless liquid
Density	1.6770 g/mL
Boiling point	82 °C (180 °F; 355 K)
Solubility in water	Reacts to form Triflic acid
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H272, H302, H314, H335
NFPA 704 (fire diamond)	4 0 3 W; OX
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

Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF₃SO₂)₂O. It is the acid anhydride derived from triflic acid. This compound is a strong electrophile, useful for introducing the triflyl group, CF₃SO₂. Abbreviated Tf₂O, triflic anhydride is the acid anhydride of the superacid triflic acid, CF₃SO₂OH.^[2]^[3]

Preparation and uses

Triflic anhydride is prepared by dehydration of triflic acid using P₄O₁₀.^[2]

Triflic anhydride is useful for converting ketones into enol triflates.^[4]

In a representative application, is used to convert an imine into a NTf group.^[5] It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.^[6]^[7]

Assay

The typical impurity in triflic anhydride is triflic acid, which is also a colorless liquid. Samples of triflic anhydride can be assayed by ¹⁹F NMR spectroscopy: −72.6 ppm^[8] vs. −77.3 for TfOH (std CFCl₃).

Safety

It is an aggressive electrophile and readily hydrolyzes to the strong acid triflic acid. It is very harmful to skin and eyes.^[9]

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.
^ ^a ^b Martínez, A. G.; Subramanian, L. R.; Hanack, M. (2016). "Trifluoromethanesulfonic Anhydride". Encyclopedia of Reagents for Organic Synthesis: 1–17. doi:10.1002/047084289X.rt247.pub3. ISBN 9780470842898.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.
^ Cacchi, Sandro; Morera, Enrico; Ortar, Giorgio (2011). "Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-diene". Organic Syntheses. 88: 260. doi:10.15227/orgsyn.088.0260.
^ Baker, T. J.; Tomioka, M.; Goodman, M. (2002). "Preparation and Use of N,N'-Di-BOC-N''-Triflylguanidine". Organic Syntheses. 78: 91. doi:10.15227/orgsyn.078.0091.
^ McWilliams, J. C.; Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D. "Preparation of n-Butyl 4-Chlorophenyl Sulfide". Organic Syntheses. 79: 43. doi:10.15227/orgsyn.079.0043{{cite journal}}: CS1 maint: multiple names: authors list (link).
^ Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. (1999). "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Organic Syntheses. 76: 6. doi:10.15227/orgsyn.076.0006.
^ 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.
^ "MSDS - 176176". www.sigmaaldrich.com. Retrieved 2020-08-09.