6075. Methyl Fluorosulfonate

Nomenclature

CAS number: 421-20-5
Sulfuryl fluoride methyl ester; fluorosulfuric acid methyl ester; methyl fluorosulfate; methyl fluosulfonate; Magic Methyl.
CH3FO3S; mol wt 114.10.
C 10.53%, H 2.65%, F 16.65%, O 42.07%, S 28.10%.

Description and references

Prepn from dimethyl ether and fluosulfonic acid: J. Meyer, G. Schramm, Z. Anorg. Allg. Chem. 206, 24 (1932) DOI. Electrochemical prepn: J. P. Coleman, D. Pletcher, Tetrahedron Lett. 15, 147 (1974) DOI. Synthetic application as methylating agent: M. G. Ahmed et al., Chem. Commun. 1968, 1533 DOI. Toxicity study: M. Hite et al., Am. Ind. Hyg. Assoc. J. 40, 600 (1979) DOI PubMed. Review: R. W. Alder, Chem. Ind. (London) 1973, 983-986.

Chemical structure

Properties

Volatile liq, bp 92-94°, mp 95°. Poisonous. d 1.412. nD20 1.3326. Good solvent for most organic compounds. Proton NMR absorption at tau 5.88. LD50 orally in mice: <112 mg/kg; LC50 1 hr for rats: 5-6 ppm (Hite).

Caution

Extremely toxic to humans. Exposure can cause fatal pulmonary edema. See: D. M. W. vanden Ham, D. van der Meer, Chem. Eng. News 54, 5 (Aug. 30, 1976); eidem, Chem. Br. 1976, 362.

Use

In organic synthesis as methylating agent.