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Methyl fluorosulfonate

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Methyl fluorosulfonate
Names
IUPAC name Methyl fluorosulfonate
Other names Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.369 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CH3FO3S/c1-5-6(2,3)4/h1H3Key: MBXNQZHITVCSLJ-UHFFFAOYSA-N
  • InChI=1/CH3FO3S/c1-5-6(2,3)4/h1H3Key: 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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, 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. (1979). "Acute toxicity of methyl fluorosulfonate (Magic Methyl)". AIHA Journal. 40 (7): 600–603. doi:10.1080/00028897708984416. PMID 484483. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
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