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| Names | |
|---|---|
| Preferred IUPAC name Methyl trifluoromethanesulfonate | |
| Other names Trifluoromethanesulfonic acid, methyl ester Triflic acid, methyl ester, methyl triflate | |
| Identifiers | |
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3D model (JSmol) | |
| ChemSpider |
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| ECHA InfoCard | 100.005.793 |
| EC Number |
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| UNII | |
| UN number | 2924 |
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| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Methyl trifluoromethanesulfonate, also commonly calledmethyl triflate and abbreviatedMeOTf, is theorganic compound with theformulaCF3SO2OCH3. It is a colourless liquid which finds use in organic chemistry as a powerfulmethylating agent.[2] The compound is closely related tomethyl 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]
Methyl triflate is commercially available, however it may also be prepared in the laboratory by treatingdimethyl sulfate with triflic acid.[4]
Upon contact with water, methyl triflate loses its methyl group, forming triflic acid and methanol:
One ranking of methylating agents is(CH3)3O+ > CF3SO2OCH3 ≈ FSO2OCH3 >(CH3)2SO4 >CH3I.[4] Methyl triflate will alkylate many functional groups which are very poor nucleophiles such asaldehydes,amides, andnitriles. It does not methylate benzene or the bulky2,6-di-tert-butylpyridine.[2] Its ability to methylateN-heterocycles is exploited in certaindeprotection schemes.[5]
Methyl triflate initiates theliving cationic polymerization oflactide[6] and other lactones includingβ-propiolactone,ε-caprolactone andglycolide.[7]
Cyclic carbonates liketrimethylene carbonate and neopentylene carbonate (5,5-dimethyl-1,3-dioxan-2-one) can be polymerized to the corresponding polycarbonates.[8] 2-alkyl-2-oxazolines, for example2-ethyl-2-oxazoline, are also polymerized to poly(2-alkyloxazoline)s.[9]
Carbon-11 methyl triflate ([11C]MeOTf[10]), or methyl triflate containing the carbon-11 isotope, is commonly used inradiochemistry to synthesize radioactively labeled compounds that can be traced in living organisms usingpositron emission tomography (PET). For example, [11C]MeOTf has been used extensively in the production ofPittsburgh Compound B, which first allowed β-amyloid plaques to be imaged in a living brain.
