|Preferred IUPAC name
Trifluoromethanesulfonic acid, methyl ester
Triflic acid, methyl ester, methyl triflate
3D model (JSmol)
CompTox Dashboard (EPA)
|Melting point||-64 °C (-83 °F; 209 K)|
|Boiling point||100 °C (212 °F; 373 K)|
|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).
|what is ?)(|
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. The compound is closely related to methyl fluorosulfonate (FSO2OCH3). Although there has yet to be a reported human fatality, while several cases were reported for methyl fluorosulfonate (LC50 (rat, 1 h) = 5 ppm), methyl triflate is expected to have similar toxicity based on available evidence.
The compound hydrolyzes violently upon contact with water:
One ranking of methylating agents is (CH3)3O+ > CF3SO2OCH3 ? FSO2OCH3 > (CH3)2SO4 > CH3I. Methyl triflate will alkylate many functional groups which are very poor nucleophiles such as aldehydes, amides, and nitriles. It does not methylate benzene or the bulky 2,6-di-tert-butylpyridine. Its ability to methylate N-heterocycles is exploited in certain deprotection schemes.
Cyclic carbonates like trimethylene carbonate and neopentylene carbonate (5,5-dimethyl-1,3-dioxan-2-one) can be polymerized to the corresponding polycarbonates. 2-alkyl-2-oxazolines, for example 2-ethyl-2-oxazoline, are also polymerized to poly(2-alkyloxazoline)s.