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'''Methyl fluorosulfonate''', (also known as '''magic methyl''', a name coined by ]) has the chemical formula F-SO<sub>2</sub>-OCH<sub>3</sub>. It is prepared by distillation of an equimolar mixture of ] and ], and used as a powerful (about four orders of magnitude more reactive than ]) ] reagent. Since it will just as readily methylate the experimenting scientist<ref>{{cite journal | author = Hite, M. | coauthors = Rinehart, W.; Braun, W.; Peck, H. | year = 1979 | title = Acute toxicity of methyl fluorosulfonate (Magic Methyl) | journal = AIHA Journal | volume = 40 | issue = 7 | pages = 600–603 | pmid = 484483 | doi = 10.1080/00028897708984416}}</ref>, 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. '''Methyl fluorosulfonate''', (also known as '''magic methyl''', a name coined by ]) has the chemical formula F-SO<sub>2</sub>-OCH<sub>3</sub>. It is prepared by distillation of an equimolar mixture of ] and ], and used as a powerful (about four orders of magnitude more reactive than ]) ] reagent. Since it will just as readily methylate biological tissues<ref>{{cite journal | author = Hite, M. | coauthors = Rinehart, W.; Braun, W.; Peck, H. | year = 1979 | title = Acute toxicity of methyl fluorosulfonate (Magic Methyl) | journal = AIHA Journal | volume = 40 | issue = 7 | pages = 600–603 | pmid = 484483 | doi = 10.1080/00028897708984416}}</ref>, 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.




Revision as of 23:17, 9 December 2010

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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