Methyl trifluoromethansulfonate

Methyl triflate
Names
IUPAC name
Methyl trifluoromethanesulfonate
Other names
Trifluoromethanesulfonic acid, methyl ester
Triflic acid, methyl ester, methyl triflate
Identifiers
333-27-7 YesY
ChemSpider 9153 YesY
Jmol interactive 3D Image
PubChem 9526
Properties
C2H3F3O3S
Molar mass 164.10 g/mol
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
Main hazards Corrosive
R-phrases R10, R34
S-phrases S26, S36/37/39, S45
Flash point 38 °C (100 °F; 311 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Methyl trifluoromethanesulfonate, commonly abbreviated MeOTf, is the organic compound with the formula CF3SO2OCH3. It is a colourless liquid that is a very powerful (and very dangerous) methylating reagent in chemistry.[1]

Reactivity

The compound hydrolyzes violently upon contact with water:

CF3SO2OCH3 + H2O → CF3SO2OH + CH3OH

This compound is closely related to methyl fluorosulfonate (FSO2OCH3), which is an older and less common reagent. These compounds alkylate faster and with wider range of substrates than traditional methylating agents such as methyl iodide. One ranking of alkylating agents is (CH3)3O+ > CF3SO2OCH3 ~ FSO2OCH3 > (CH3)2SO4> CH3I. It will alkylate many functional groups that are only weakly basic such as aldehydes, amides, and nitriles. It does not methylate benzene or the bulky 2,6-di-tert-butylpyridine.[1] Its ability to methylate N-heterocycles is exploited in certain deprotection schemes.[2]

See also

References

  1. 1 2 Roger W. Alder, Justin G. E. Phillips, Lijun Huang, Xuefei Huang, "Methyltrifluoromethanesulfonate" Encyclopedia of Reagents for Organic Synthesis 2005 John Wiley & Sons, doi:10.1002/047084289X.rm266m.pub2
  2. ↑ Albert I. Meyers and Mark E. Flanagan. (1998). "2,2'-Dimethoxy-6-formylbiphenyl". Org. Synth.; Coll. Vol. 9, p. 258
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