Methyl fluorosulfonate

Methyl fluorosulfonate
Names
	IUPAC name Methyl fluorosulfonate
	Other names Methyl fluorosulphonate; Fluorosulfonic acid, methyl ester; Methyl fluorosulphate; Magic methyl;
Identifiers
CAS Number	421-20-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	9486 ;
ECHA InfoCard	100.006.369
PubChem CID	9870;
UNII	N015VFJ94Z ;
CompTox Dashboard (EPA)	DTXSID8073180 ;
	InChI InChI=1S/CH3FO3S/c1-5-6(2,3)4/h1H3 Key: MBXNQZHITVCSLJ-UHFFFAOYSA-N ; InChI=1/CH3FO3S/c1-5-6(2,3)4/h1H3 Key: MBXNQZHITVCSLJ-UHFFFAOYAW;
	SMILES FS(=O)(=O)OC;
Properties
Chemical formula	CH3FO3S
Molar mass	114.09 g·mol−1
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 Because of its extreme toxicity, it has largely been replaced by the related reagent methyl trifluoromethanesulfonate.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

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

It is acutely toxic[1] by inhalation with LC₅₀ (rat, 1 hour) of about 5 ppm, and several cases of poisoning resulting in death from pulmonary edema have been reported.[3]

References

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.CS1 maint: uses authors parameter (link)
Stang, Peter J.; Hanack, Michael; Subramanian, L. R. (1982). "Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry". Synthesis. 1982 (02): 85–126. doi:10.1055/s-1982-29711. ISSN 0039-7881.
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.

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[stang-1] 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.CS1 maint: uses authors parameter (link)

[Stang-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. doi:10.1055/s-1982-29711. ISSN 0039-7881.

[3] 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.