Methyl fluorosulfonate

Methyl fluorosulfonate
Names
IUPAC name
Methyl fluorosulfonate
Other names
Methyl fluorosulphonate; fluorosulfonic acid; methyl ester; methyl fluorosulphate; magic methyl
Identifiers
421-20-5 YesY
ChemSpider 9486 YesY
Jmol interactive 3D Image
PubChem 9870
Properties
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).
YesY verify (what is YesYN ?)
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.
This article is issued from Wikipedia - version of the Monday, July 13, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.