Methyl trifluoromethanesulfonate
chemical compound
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, 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.
Synthesis
Methyl triflate is commercially available, however it may also be prepared in the laboratory by using dimethyl sulfate to methylate triflic acid.
CF3SO2OH + (CH3O)2SO2 → CF3SO2OCH3 + CH3OSO2OH
Reactivity
Hydrolysis
Upon contact with water, methyl triflate loses its methyl group, forming triflic acid and methanol:
CF3SO2OCH3 + H2O → CF3SO2OH + CH3OH
Methylation
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.
Cationic polymerization
Methyl triflate initiates the living cationic polymerization of lactide and other lactones including β-propiolactone, ε-caprolactone and glycolide.
Cyclic carbonates like trimethylene carbonate and neopentylene carbonate (5,5-dimethyl-1,3-dioxan-2-one) can be polymerized to the corresponding polycarbonates.
This brief starts where responsible research should: with the source description of “Methyl trifluoromethanesulfonate” as chemical compound. Everything that follows is an evidence route, not borrowed authority.
Why this record matters
The subject matters to the science & nature register because the source frames it as chemical compound. Its deeper value depends on whether names, dates, institutions and citations support that framing.
The date and method of observation matter as much as the stated conclusion, especially where classification or consensus has changed. The source revision retrieved here is dated Jun 18, 2026. The linked authority identifier is Q907614. None of the 0 selected statements returned an explicit reference.
Scientific names, classifications and consensus can change while older terminology persists in catalogues and historical literature. The source lead contains qualifying language; that uncertainty should survive quotation, summary and reuse. Authority statements aid reconciliation but still require their own references, qualifiers and ranks to be checked.
How to read it
Check terminology, classification and the date of the cited evidence. Scientific names and technical consensus can change while older records retain historical value.
- Current terminology
- Classification context
- Finding cited technical literature
Primary datasets, specimen catalogues, standards bodies and the most recent peer-reviewed literature.
Three-step research path
- Establish the record: confirm the title “Methyl trifluoromethanesulfonate”, its source revision and the description used here.
- Expand the search: follow Methyl trifluoromethanesulfonate primary sources, Methyl trifluoromethanesulfonate archive and Methyl research across catalogues and specialist indexes.
- Test the account: compare the strongest cited source with the responsible institution’s current record and note any disagreement.
Questions for further research
- Which source most directly establishes the central claim about “Methyl trifluoromethanesulfonate”?
- Is the terminology current, historical or disputed?
- Which observation, specimen, dataset or publication supports the account?
Search terms from this dossier
This entry incorporates text from “Methyl trifluoromethanesulfonate” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.