Methyl fluorosulfonate

Methyl fluorosulfonate

Names
IUPAC name Methyl fluorosulfonate
Other names Methyl fluorosulphonate; fluorosulfonic acid; methyl ester; methyl fluorosulphate; magic methyl
Identifiers
CAS Number	421-20-5
ChemSpider	9486
Jmol interactive 3D	Image
PubChem	9870
InChI InChI=1S/CH3FO3S/c1-5-6(2,3)4/h1H3 Key: MBXNQZHITVCSLJ-UHFFFAOYSA-N InChI=1/CH3FO3S/c1-5-6(2,3)4/h1H3 Key: MBXNQZHITVCSLJ-UHFFFAOYAW
SMILES FS(=O)(=O)OC
Properties
Chemical formula	CH3O3FS
Molar mass	114.09 g/mol
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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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 methylating reagent (about four orders of magnitude more reactive than methyl iodide). 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

1. 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.