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Trifluoromethanesulfonic anhydride

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Trifluoromethanesulfonic anhydride
Skeletal formula of triflic anhydride
Names
Preferred IUPAC name Trifluoromethanesulfonic anhydride
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.016 Edit this at Wikidata
EC Number
  • 206-616-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8Key: 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
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 GHS03: OxidizingGHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H272, H302, H314, H335
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazard W+OX: Reacts with water in an unusual or dangerous manner AND is oxidizer
4 0 3W
OX
Safety data sheet (SDS) Fisher MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Preparation and uses

Triflic anhydride is prepared by dehydration of triflic acid using P4O10.

Triflic anhydride is useful for converting ketones into enol triflates.

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.

Assay

The typical impurity in triflic anhydride is triflic acid, which is also a colorless liquid. Samples of triflic anhydride can be assayed by F NMR spectroscopy: −72.6 ppm 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.

See also

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. ^ 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)
  3. 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.
  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.
  5. 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.
  6. 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).
  7. 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.
  8. 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.
  9. "MSDS - 176176". www.sigmaaldrich.com. Retrieved 2020-08-09.
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