- Methyl fluorosulfonate
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Methyl fluorosulfonate Methyl fluorosulfonateOther namesMethyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphateIdentifiers CAS number 421-20-5 PubChem 9870 ChemSpider 9486 Jmol-3D images Image 1 - FS(=O)(=O)OC
Properties Molecular formula CH3O3FS Molar mass 114.09 g/mol Density 1.45 g/mL Boiling point 93 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Methyl fluorosulfonate, (also known as magic methyl, a name coined by George Olah) has the chemical formula F-SO2-OCH3. It is prepared by distillation of an equimolar mixture of fluorosulfonic acid and dimethyl sulfate, and used as a powerful (about four orders of magnitude more reactive than methyl iodide) methylating reagent. Since it will just as readily methylate biological tissues[1], it is acutely toxic (LC50 (rat) ~ 5 ppm), causing irritation of the airways and pulmonary edema, presumably by methylation of lipids in the cell membranes. Its use as a methylating reagent is banned by many organisations as a result.
References
- ^ Hite, M.; Rinehart, W.; Braun, W.; Peck, H. (1979). "Acute toxicity of methyl fluorosulfonate (Magic Methyl)". AIHA Journal 40 (7): 600–603. doi:10.1080/00028897708984416. PMID 484483.
Categories:- Methylating agents
- Methyl esters
- Sulfonate esters
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