Methyl trifluoromethanesulfonate

Methyl trifluoromethanesulfonate
Structural formula of methyl triflate
Ball-and-stick model of methyl triflate
Names
Preferred IUPAC name
Methyl trifluoromethanesulfonate
Other names
Trifluoromethanesulfonic acid, methyl ester
Triflic acid, methyl ester, methyl triflate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.793 Edit this at Wikidata
EC Number
  • 206-371-7
UNII
UN number 2924
  • InChI=1S/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3 checkY
    Key: OIRDBPQYVWXNSJ-UHFFFAOYSA-N checkY
  • InChI=1/C2H3F3O3S/c1-8-9(6,7)2(3,4)5/h1H3
    Key: OIRDBPQYVWXNSJ-UHFFFAOYAL
  • COS(=O)(=O)C(F)(F)F
Properties
C2H3F3O3S
Molar mass 164.10 g·mol−1
Appearance Colourless Liquid
Density 1.496 g/mL
Melting point −64 °C (−83 °F; 209 K)
Boiling point 100 °C (212 °F; 373 K)
Hydrolyzes
Hazards[1]
Occupational safety and health (OHS/OSH):
Main hazards
Corrosive
GHS labelling:
Danger
H226, H301, H311, H314, H330
P210, P233, P303+P361+P353, P304+P340+P310, P305+P351+P338, P380
Flash point 38 °C (100 °F; 311 K)
Related compounds
Related compounds
Methyl fluorosulfonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl trifluoromethanesulfonate, also commonly called methyl triflate and abbreviated MeOTf, is the organic compound with the formula CF3SO2OCH3. It is a colourless liquid which finds use in organic chemistry as a powerful methylating agent.[2] The compound is closely related to methyl fluorosulfonate (FSO2OCH3). Although there has yet to be a reported human fatality, several cases were reported for methyl fluorosulfonate (LC50 (rat, 1 h) = 5 ppm), and methyl triflate is expected to have similar toxicity based on available evidence.[3][verification needed]

  1. ^ "Methyl trifluoromethanesulfonate". Sigma-Aldrich. Retrieved 31 October 2021.
  2. ^ Alder, Roger W.; Phillips, Justin G. E.; Huang Lijun; Huang Xuefei (2005). "Methyltrifluoromethanesulfonate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm266m.pub2. ISBN 0471936235.
  3. ^ Alder, R. W.; Sinnott, M. L.; Whiting, M. C.; Evans, D. A. (1978). "Hazards of powerful methylating agents". Chemistry in Britain. Vol. 14, no. 7. p. 324. Miscited as ——— (1976) Chem. Eng. News, vol. 54, no. 36, p. 56 in Alder et al. 2005