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 Because of its extreme toxicity, it has largely been replaced by the related reagent methyl trifluoromethanesulfonate.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 edit
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 edit
Similar to phosgene, it is acutely toxic[1] by inhalation, with an LC50 (rat, 1 hour) of about 5 ppm. Several cases of poisoning resulting in death from pulmonary edema have been reported.[3]
References edit
- ^ a b Meyer, Julius; Schramm, Georg (1932). "Ester der Fluorsulfonsäure (Esters of fluorosulfonic acid)". Zeitschrift für Anorganische und Allgemeine Chemie. 206: 24–30. doi:10.1002/zaac.19322060103.
- ^ Stang, Peter J.; Hanack, Michael; Subramanian, L. R. (1982). "Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry". Synthesis. 1982 (2): 85–126. doi:10.1055/s-1982-29711. ISSN 0039-7881.
- ^ 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.