Synthesis of chloromethyl chloroformate

Preparation of chloromethyl chloroformate

Alternative Names: chloromethyl carbonochloridate; chloromethylchloroformate; chloroformic acid chloromethyl ester

Preparation of chloromethyl chloroformate (chloromethyl carbonochloridate; chloroformic acid chloromethyl ester)

Preparation of chloromethyl chloroformate (chloromethyl carbonochloridate; chloroformic acid chloromethyl ester)

100 g methyl formate are placed in a 250 ml flask fitted with a reflux condenser and a glass inlet tube for chlorine, and the whole weighed. The contents of the flask are heated to boiling and then a current of chlorine introduced, exposing the reacting substances to direct sunlight as far as possible, or to the light from a 500-watt lamp. By properly regulating the temperature and the addition of the chlorine and occasionally weighing the flask and its contents it is possible to obtain monochloro-derivative. The reaction product is fractionally distilled under reduced pressure. Chloromethyl chloroformate is a mobile, colorless liquid with an irritating odor, which boils at 106.5-107° C at ordinary pressure and at 52.5-53°/100 mm, d=1.465 g/ml.

J. prakt. Chem., 1887, 36, 213-305; Bull. soc. chim., 1920, 27, 97; Rev. prod, chim., 1922, 25, 685;
The war gases chemistry and analysis, by M. Sartory, 102, 1939

IUPAC Name

chloromethyl carbonochloridate

InChI

InChI=1S/C2H2Cl2O2/c3-1-6-2(4)5/h1H2

InChI Key

JYWJULGYGOLCGW-UHFFFAOYSA-N

Canonical SMILES

C(OC(=O)Cl)Cl

Depositor-Supplied Synonyms

Chloromethyl chloroformate, chloromethyl carbonochloridate, 22128-62-7, chloromethylchloroformate, JYWJULGYGOLCGW-UHFFFAOYSA-N, Chloroformic Acid Chloromethyl Ester, Carbonochloridic acid, chloromethyl ester, Palite, chlormethylchlorocarbonat, AC1L1XPS, chloromethyl chlorocarbonate, 1-chloromethyl chloroformate, AC1Q3GD3, SCHEMBL27366, 23181_ALDRICH, 23181_FLUKA, CTK1A6574, MolPort-003-928-236, EINECS 244-793-3, 1218AB, UN2745, ZINC04521315, Chlorocarbonic acid chloromethyl ester, AKOS005259776, chloroformic acid 1-chloromethyl ester, NE11190, UN 2745, Formic acid, chloro-, chloromethyl ester, AK122315, DB-045811, FT-0623671, Chloromethyl chloroformate [UN2745] [Poison], I14-8772, 3B3-011312

Removed Synonyms

CID62754, c1396

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