Synthesis of methyl fluorosulfonate

Preparation of methyl fluorosulfonate (methyl fluorosulfate; magic methyl; methyl fluorosulphonate; methyl fluorosulphate)

Preparation of methyl fluorosulfonate (methyl fluorosulfate; magic methyl; methyl fluorosulphonate; methyl fluorosulphate)

Preparation of methyl fluorosulfonate (methyl fluorosulfate; magic methyl; methyl fluorosulphonate; methyl fluorosulphate)

10 ml fluorosulfonic acid are placed in a wash-bottle and a current of dry dimethyl ether, obtained by heating 1-3 parts methanol with 2 parts concentrated sulfuric acid to 140° C is passed in. The methyl ether is absorbed and reacts immediately. For safety, a second wash-bottle should be inserted containing a further 10 ml fluorosulfonic acid, and after this it is best to introduce another containing concentrated sulfuric acid. After 3 hours, when the fluorosulfonic acid in the first bottle absorbs no more methyl ether, the product is distilled under reduced pressure. At a pressure of 160 mm methyl fluorosulfonate distils at 45° C. Methyl fluorosulfonate is a liquid with an ethereal odor, boiling at 92° C at ordinary pressure. It has a d=1.427 g/ml at 16° C and attacks the glass. Methyl fluorosulfonate is not miscible with water, but is rapidly saponified, especially in the presence of alkalies or acids.

Z. Anorg. Chem., 1932, 206, 27.

The war gases chemistry and analysis,by M. Sartory, 266, 1939

IUPAC Name

fluorosulfonyloxymethane

InChI

InChI=1S/CH3FO3S/c1-5-6(2,3)4/h1H3

InChI Key

MBXNQZHITVCSLJ-UHFFFAOYSA-N

Canonical SMILES

COS(=O)(=O)F

MeSH Synonyms

methyl fluorosulfate, methyl fluorosulfonate

Depositor-Supplied Synonyms

METHYL FLUOROSULFONATE, Methyl fluorosulfate, Magic methyl, 421-20-5, Methyl fluorosulphonate, Methyl fluorosulphate, Methyl fluosulfonate, methylfluorosulfonate, fluorosulfonyloxymethane, Fluorosulfuric acid, methyl ester, UNII-N015VFJ94Z, CCRIS 1135, N015VFJ94Z, HSDB 4375, EINECS 207-004-3, BRN 1098714, methyl fluoridosulfate, ACMC-20akfc, methyl fluoranesulfonate, Methyl sulphurofluoridate, AC1L1U0A, [(fluorosulfonyl)oxy]methane, SCHEMBL526480, Sulfuryl fluoride,methyl ester, Fluorosulfonic Acid Methyl Ester, Fluorosulfuric Acid Methyl Ester, fluorosulphonic acid methyl ester, CTK4I5729, fluorosulfonic acid, methyl ester, MBXNQZHITVCSLJ-UHFFFAOYSA-N, PC5095, AKOS006221871, KB-54781, LS-69356, TC-166143, F0238, FT-0626482, fluoridosulfuric acid (HSO_3_), methyl ester, InChI=1/CH3FO3S/c1-5-6(2,3)4/h1H, A825774, 3B3-052439, I14-101701

Removed Synonyms

CID9870, 4-01-00-01251 (Beilstein Handbook Reference)

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