Methyl fluorosulfonate

Methyl fluorosulfonate
IUPAC name Methyl fluorosulfonate
Other names Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate
Identifiers
CAS number	421-20-5
PubChem	9870
ChemSpider	9486 Y
Jmol-3D images	Image 1
SMILES FS(=O)(=O)OC
InChI InChI=1S/CH3FO3S/c1-5-6(2,3)4/h1H3 Y Key: MBXNQZHITVCSLJ-UHFFFAOYSA-N Y InChI=1/CH3FO3S/c1-5-6(2,3)4/h1H3 Key: MBXNQZHITVCSLJ-UHFFFAOYAW
Properties
Molecular formula	CH3O3FS
Molar mass	114.09 g/mol
Density	1.45 g/mL
Boiling point	93 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 (about four orders of magnitude more reactive than methyl iodide) methylating reagent. 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.