Trifluoromethanesulfonic anhydride

Trifluoromethanesulfonic anhydride
Skeletal formula of triflic anhydride
Names
Preferred IUPAC name
Trifluoromethanesulfonic anhydride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.016 Edit this at Wikidata
EC Number
  • 206-616-8
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
Appearance colourless liquid
Density 1.6770 g/mL
Boiling point 82[1] °C (180 °F; 355 K)
Reacts to form Triflic acid
Hazards
GHS labelling:
GHS03: OxidizingGHS05: CorrosiveGHS07: Exclamation mark
Danger
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
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]

  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.