Methyl fluorosulfonate
Chemical compound
From Wikipedia, the free encyclopedia
Methyl fluorosulfonate, also known as magic methyl, is the organic compound with the formula FSO2OCH3. It is a colorless liquid that is used as a strong methylating agent in organic synthesis. Because of several fatal industrial accidents involving this compound, it has largely been replaced by the related reagent methyl trifluoromethanesulfonate.
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| Names | |
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| Preferred IUPAC name
Methyl sulfurofluoridate | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.006.369 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| CH3FO3S | |
| Molar mass | 114.09 g·mol−1 |
| Density | 1.45 g/mL |
| Boiling point | 93 °C (199 °F; 366 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
It is prepared by distillation of an equimolar mixture of fluorosulfonic acid and dimethyl sulfate. It was originally produced by the reaction of methanol with fluorosulfonic acid.[1]
Methyl fluorosulfonate is a highly electrophilic reagent for methylation. It is ranked as less powerful than methyl trifluoromethanesulfonate.[2]
Toxicity
Toxicity of this reagent is equivalent to that of phosgene with an inhaled LC50 (rat, 1 hour) of about 5 ppm. Several cases of poisoning resulting in death from pulmonary edema have been reported.[3]