Trifluoromethanesulfonic anhydride

Last updated
Trifluoromethanesulfonic anhydride
Skeletal formula of triflic anhydride Triflic-anhydride-2D.png
Skeletal formula of triflic anhydride
Trifluoromethanesulfonic anhydride Ball and Stick.png
Trifluoromethanesulfonic anhydride Space Fill.png
Names
Preferred IUPAC name
Trifluoromethanesulfonic anhydride
Identifiers
3D model (JSmol)
1813600
ChEBI
ChemSpider
ECHA InfoCard 100.006.016 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-616-8
PubChem CID
UNII
  • InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
    Key: WJKHJLXJJJATHN-UHFFFAOYSA-N
  • C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
Properties
C2F6O5S2
Molar mass 282.13 g·mol−1
Appearancecolourless liquid
Density 1.6770 g/mL
Boiling point 82 [1]  °C (180 °F; 355 K)
Reacts to form Triflic acid
Hazards
GHS labelling:
GHS-pictogram-rondflam.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H272, H302, H314, H335
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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
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).
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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]

Contents

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]

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. 1 2 Martínez, A. G.; Subramanian, L. R.; Hanack, M. (2016). "Trifluoromethanesulfonic Anhydride". Encyclopedia of Reagents for Organic Synthesis. pp. 1–17. doi:10.1002/047084289X.rt247.pub3. ISBN   9780470842898.{{cite book}}: 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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