Synthesis of methyl chloroformate

Preparation of methyl chloroformate

Methyl chloroformate prepared by reacting methyl alcohol with phosgene.

Preparation of methyl chloroformate

Preparation of methyl chloroformate

A side product (methyl carbonate) could be formed if the temperature is not kept rather low and phosgene is not used in excess:

Formation of methyl carbonate

Formation of methyl carbonate

To a reaction flask fitted with a dropping-funnel, a tube to introduce the gaseous phosgene and an exit tube a 10 ml of methyl chloroformate is placed. The reaction flask is cooled to 0° C and the current of phosgene containing no chlorine is bubbled in. About one-third of reaction flask is filled with methanol from the dropping-funnel all at once. When the phosgene gas is no longer being absorbed additional portion of a fresh methanol is added to the reaction mixture.  As soon as the reaction is complete, methyl chloroformate is transferred to a separatory funnel containing cold water. The heavier layer which separates from the aqueous layer is washed twice with cold water, dried over calcium chloride and fractionally distilled. The fraction passing over between 69-72 °C is collected. The yield of methyl chloroformate is about 70% of theory.

The war gases chemistry and analysis, by M. Sartory, 102, 1939.

IUPAC Name

methyl carbonochloridate

InChI

InChI=1S/C2H3ClO2/c1-5-2(3)4/h1H3

InChI Key

XMJHPCRAQCTCFT-UHFFFAOYSA-N

Canonical SMILES

COC(=O)Cl

MeSH Synonyms

methyl chlorocarbonate, methyl chloroformate

Depositor-Supplied Synonyms

METHYL CHLOROFORMATE, Methyl chlorocarbonate, 79-22-1, methyl carbonochloridate, Carbonochloridic acid, methyl ester, Methoxycarbonyl chloride, Chloroformic acid methyl ester, Methyl chloridocarbonate, Metilcloroformiato, RCRA waste number U156, Formic acid, chloro-, methyl ester, K-Stoff, Methylchloorformiaat, Chlorocarbonic acid methyl ester, Chloroformiate de methyle, Chlorocarbonate de methyle, TL 438, RCRA waste no. U156, Methylchloorformiaat [Dutch], Metilcloroformiato [Italian], Chlorameisensaeure methylester, HSDB 1116, Methylester kyseliny chlormravenci, Methylester kyseliny chloruhlicite, XMJHPCRAQCTCFT-UHFFFAOYSA-N, Chloroformiate de methyle [French], Chlorocarbonate de methyle [French], EINECS 201-187-3, UN1238, Chlorameisensaeure methylester [German], BRN 0605437, Methylester kyseliny chlormravenci [Czech], Methylester kyseliny chloruhlicite [Czech], MCF, methyl chloroformat, methyl chioroformate, methyl-chloroformate, sJPhEaDIMsP@, methylchlorocarbonate, methyl chloroforrnate, methyl chloroform ate, methoxycarbonylchloride, methylcarbonochloridate, methyl carbonchloridate, PubChem15319, chloro(methoxy)methanone, Methyl carbonochloridoate, AC1L1MUY, UNII-RC6VA8OB2N, DSSTox_CID_4185, Methyl chloridocarbonate #, RC6VA8OB2N, AC1Q3GC5, DSSTox_RID_77321, DSSTox_GSID_24185, M35304_ALDRICH, KSC377C3F, ACMC-20a487, AC1Q44G3, chloro formic acid methyl ester, CHEMBL3182300, 23211_FLUKA, CTK2H7132, XMJHPCRAQCTCFT-UHFFFAOYSA-, Chlorocarbonic acid, methyl ester, MolPort-001-791-964, BB_SC-7075, Tox21_200841, ANW-56405, AR-1J5772, BBL011482, STL146594, ZINC03860600, AKOS000121088, MCULE-8022274771, UN 1238, CAS-79-22-1, NCGC00248847-01, NCGC00258395-01, AN-23984, BC225650, BP-31038, CJ-10868, KB-54745, LS-52216, Methyl chloroformate [UN1238] [Poison], Methyl chloroformate [UN1238] [Poison], TR-031637, FT-0623664, InChI=1/C2H3ClO2/c1-5-2(3)4/h1H3, 17478-EP2269993A1, 17478-EP2270006A1, 17478-EP2272516A2, 17478-EP2272841A1, 17478-EP2275404A1, 17478-EP2284169A1, 17478-EP2287161A1, 17478-EP2287162A1, 17478-EP2289893A1, 17478-EP2289897A1, 17478-EP2292595A1, 17478-EP2298772A1, 17478-EP2305649A1, 17478-EP2305658A1, 17478-EP2305684A1, 17478-EP2308833A2, 17478-EP2308838A1, 17478-EP2308839A1, 17478-EP2308841A2, 17478-EP2308857A1, 17478-EP2308858A1, 17478-EP2311816A1, 17478-EP2311817A1, 17478-EP2311824A1, 17478-EP2314578A1, 17478-EP2314586A1, 3B4-1355, I14-2768

Removed Synonyms

METHYLCHLOROFORMATE, CID6586, c0180, 4-03-00-00023 (Beilstein Handbook Reference), 83616-19-7

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