| Methyl fluorosulfonate | |
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| IUPAC name |
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| Other names | Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate |
| Identifiers | |
| CAS number | [] |
| Properties | |
| Molecular formula | CH3O3FS |
| Molar mass | 114.09 g/mol |
| Density | 1.45 g/mL |
| Boiling point |
93 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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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 used as a powerful (about four orders of magnitude more reactive than methyl iodide) methylating reagent.
Methyl fluorosulfonate is prepared by distillation from an equimolar mixture of fluorosulfonic acid and dimethyl sulfate.
The compound is acutely toxic (LC50 (rat) ~ 5 ppm), causing irritation of the respiratory tract and pulmonary edema, presumably through alkylation of lipids in the cell membranes.[1]
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:. PMID 484483.
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