Methyl fluorosulfonate
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| Names | |
|---|---|
| IUPAC name
Methyl fluorosulfonate
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| Other names
Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate
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| Identifiers | |
| ECHA InfoCard | 100.006.369 |
CompTox Dashboard (EPA)
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| Properties | |
| CH3O3FS | |
| Molar mass | 114.09 g/mol |
| Density | 1.45 g/mL |
| Boiling point | 93 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 the experimenting scientist[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. (1979). "Acute toxicity of methyl fluorosulfonate (Magic Methyl)". AIHA Journal. 40 (7): 600–603. doi:10.1080/00028897708984416. PMID 484483.
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