Synthesis of perchloromethyl mercaptan

Preparation of perchloromethyl mercaptan

Perchloromethyl mercaptan is prepared by reaction of chlorine with carbon disulfide.

Preparation of perchloromethyl mercaptan

Preparation of perchloromethyl mercaptan

To the round bottom flask fitted with a reflux condenser 75 g carbon disulfide and 0.3 g iodine are placed. While the flask is being externally cooled with ice-water, a current of dry chlorine is passed in for several hours. Chlorination reaction could be accelerated by exposing the contents of the flask to diffused daylight. When the volume of the liquid has been approximately doubled (and its weight has reached about 150-160 g) the current of chlorine is stopped and the mixture allowed to stand overnight. The next day reaction mixture is warmed to remove an excess of carbon disulfide and carbon tetrachloride (side product). The sulfur chloride is decomposed by adding an equal volume of water to the residue and shaking vigorously. This is then distilled first in steam and then under reduced pressure at 50 mm of Hg. Perchloromethyl mercaptan is an oily, clear yellow liquid with an unpleasant odor, which boils at 148-149° C with decomposition.

The war gases chemistry and analysis, by M. Sartory, 212, 1939.

IUPAC Name

trichloromethyl thiohypochlorite

InChI

InChI=1S/CCl4S/c2-1(3,4)6-5

InChI Key

RYFZYYUIAZYQLC-UHFFFAOYSA-N

Canonical SMILES

C(SCl)(Cl)(Cl)Cl

MeSH Synonyms

perchloromethyl mercaptan, trichloromethylsulfenyl chloride

Depositor-Supplied Synonyms

Perchloromethyl mercaptan, Clairsit, Perchloromethylmercaptan, TRICHLOROMETHANESULFENYL CHLORIDE, Methanesulfenyl chloride, trichloro-, Perchloromethanethiol, (Trichloromethane)sulfenyl chloride, 594-42-3, Perchlormethylmerkaptan, Trichloromethylsulfenyl chloride, Trichloromethanesulphenyl chloride, Trichloromethane sulfenyl chloride, RCRA waste number P118, Mercaptan methylique perchlore, Trichloromethylsulphenyl chloride, Perchlorinemethylmercaptan, Thiocarbonyl tetrachloride, NSC 66404, RCRA waste no. P118, Trichloromethyl sulfochloride, Trichloromethyl sulphochloride, Trichlormethyl sulfur chloride, trichloromethyl thiohypochlorite, HSDB 886, Perchlormethylmerkaptan [Czech], HSDB 6052, (Trichloromethyl)sulfenyl chloride, Perchloro-methyl-mercaptan (DOT), RYFZYYUIAZYQLC-UHFFFAOYSA-N, Trichloromethane sulphuryl chloride, EINECS 209-840-4, SBB058912, UN1670, Mercaptan methylique perchlore [French], BRN 0506034, Methanesulfenic acid, trichloro-, chloride, chlorothio(trichloromethyl), sGPJADPHtPXbqBRuUP@, WLN: GXGGSG, AC1L1XUU, Perchloro-methyl-mercaptan, DSSTox_CID_5854, perchloro(methyl mercaptan), UNII-KK489OII9M, AC1Q3VR0, DSSTox_RID_77949, KK489OII9M, DSSTox_GSID_25854, SCHEMBL190299, Trichloromethyl sulfur chloride, trichloro(chlorosulfanyl)methane, 332895_ALDRICH, trichloromethyl sulfenyl chloride, CHEMBL3188766, RYFZYYUIAZYQLC-UHFFFAOYSA-, trichloromethane-sulfenyl chloride, MolPort-000-160-046, trichloro-methanesulphenyl chloride, trichloromethane sulphenyl chloride, NSC66404, Tox21_200422, NSC-66404, AKOS006222983, LS-1420, UN 1670, NCGC00248604-01, NCGC00257976-01, AN-46244, CAS-594-42-3, InChI=1/CCl4S/c2-1(3,4)6-5, P0740, ST51042198, Perchloromethyl mercaptan [UN1670] [Poison], Perchloromethyl mercaptan [UN1670] [Poison], 20434-91-7, 344328-67-2

Removed Synonyms

Trichloromethanethiol, Trichlorofluoromethane, Methanethiol, trichloro-, TRICHLOROMETHYL MERCAPTAN, CID11666, 4-03-00-00290 (Beilstein Handbook Reference), PCM, PMM, 75-70-7

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