Methyl fluorosulfonate

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Methyl fluorosulfonate
Methyl fluorosulfonate.png
Methyl-fluorosulfonate-3D-balls.png
Names
IUPAC name
Methyl fluorosulfonate
Other names
Methyl fluorosulphonate; fluorosulfonic acid; methyl ester; methyl fluorosulphate; magic methyl
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.369
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).
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Infobox references

Methyl fluorosulfonate, (also known as magic methyl), is the organic compound with the formula FSO2OCH3. It is a colorless liquid that is used as a strong methylating agent in organic synthesis. Because of its extreme toxicity, it has largely been replaced by the related reagent methyl trifluoromethanesulfonate.

Synthesis and reactions[edit]

It is prepared by distillation of an equimolar mixture of fluorosulfonic acid and dimethyl sulfate. It was originally produced by the reaction of methanol with fluorosulfonic acid.[1]

Methyl fluorosulfonate is a highly electrophilic reagent for methylation. It is ranked as less powerful than methyl trifluoromethanesulfonate.[2]

Toxicity[edit]

It is acutely toxic[1] with LC50 (rat) ~ 5 ppm.[3]

References[edit]

  1. ^ a b Meyer, Julius; Schramm, Georg (1932). "Ester der Fluorsulfonsäure (Esters of fluorosulfonic acid)". Zeitschrift für Anorganische und Allgemeine Chemie. 206: 24–30. doi:10.1002/zaac.19322060103. 
  2. ^ Stang, Peter J.; Hanack, Michael; Subramanian, L. R. (1982). "Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry". Synthesis. 1982 (02): 85–126. ISSN 0039-7881. doi:10.1055/s-1982-29711. 
  3. ^ Hite, M.; Rinehart, W.; Braun, W.; Peck, H. (1979). "Acute toxicity of methyl fluorosulfonate (Magic Methyl)". AIHA Journal. 40 (7): 600–603. PMID 484483. doi:10.1080/00028897708984416.