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Revision as of 13:19, 3 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit Revision as of 13:30, 3 December 2010 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WiNext edit →
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{{chembox {{chembox
| verifiedrevid = 400307250
| ImageFile = Methyl fluorosulfonate.png | ImageFile = Methyl fluorosulfonate.png
| ImageFile1 = Methyl-fluorosulfonate-3D-balls.png | ImageFile1 = Methyl-fluorosulfonate-3D-balls.png
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| OtherNames = Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate | OtherNames = Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9486 | ChemSpiderID = 9486
| InChI = 1/CH3FO3S/c1-5-6(2,3)4/h1H3 | InChI = 1/CH3FO3S/c1-5-6(2,3)4/h1H3
| InChIKey = MBXNQZHITVCSLJ-UHFFFAOYAW | InChIKey = MBXNQZHITVCSLJ-UHFFFAOYAW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CH3FO3S/c1-5-6(2,3)4/h1H3 | StdInChI = 1S/CH3FO3S/c1-5-6(2,3)4/h1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MBXNQZHITVCSLJ-UHFFFAOYSA-N | StdInChIKey = MBXNQZHITVCSLJ-UHFFFAOYSA-N
| CASNo = 421-20-5 | CASNo = 421-20-5

Revision as of 13:30, 3 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 the experimenting scientist, 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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