Synthesis of sulfur mustard

Preparation of sulfur mustard

Bis(2-chloroethyl) sulfide is prepared by bubbling ethylene through sulfur chloride.

Preparation of bis(2-chloroethyl) sulfide

Preparation of bis(2-chloroethyl) sulfide

All work MUST be done in a ventilated hood! The reaction between the ethylene and the sulfur chloride takes place in the round bottom flask fitted with gas inlet tube for ethylene, dropping funnel for sulfur chloride and outlet tube to carry off excess gas. Before reaction etlylene is washed and dried by passing through concentrated sulfuric acid, 10% sodium hydroxide and again concentrated sulfuric acid. As soon as the current of ethylene becomes steady from wash-bottles ethylene is introduced in the reaction flask, in which 20 g sulfur chloride have been previously placed. During the passage of the ethylene, a further 30 g sulfur chloride are added from the dropping-funnel in three portions.  The reaction flask is immersed in a cooled water so that the temperature of the reaction mixture does not exceed 35° C. The passage of the ethylene is continued until all the sulfur chloride has been used up. At the end of the reaction bis(2-chloroethyl) sulfide is distilled under reduced pressure, the fraction passing over between 106° and 108° C at 15 mm of Hg being collected. Dichloroethyl sulphide is an oily, colorless liquid which boils at 217.5° C and melts at 14.4° C.

The war gases chemistry and analysis, by M. Sartory, 219-220, 1939.

IUPAC Name

1-chloro-2-(2-chloroethylsulfanyl)ethane

InChI

InChI=1S/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2

InChI Key

QKSKPIVNLNLAAV-UHFFFAOYSA-N

Canonical SMILES

C(CCl)SCCCl

MeSH Synonyms

Bis(beta-chloroethyl) Sulfide, Di 2 chloroethyl Sulfide, Di-2-chloroethyl Sulfide, Dichlorodiethyl Sulfide, Gas, Mustard, Mustard Gas, Mustard, Sulfur, Mustardgas, Psoriazin, Sulfide, Di-2-chloroethyl, Sulfide, Dichlorodiethyl, Sulfur Mustard, Yellow Cross Liquid, Yperite

Depositor-Supplied Synonyms

Mustard gas, Sulfur mustard, Yperite, Iprit, Senfgas, Lost, Yellow cross liquid, Schwefel-lost, Mustard, sulfur, Distilled mustard, S-Lost, Gelbkreuz, Bis(2-chloroethyl) sulfide, Mustard vapor, S-yperite, S Mustard, Yellow cross gas, Mustard HD, Sulfur mustard gas, Dichlorodiethyl sulfide, Mustard, Psoriasin, 1,1′-Thiobis(2-chloroethane), 505-60-2, Kampstoff lost, Sulphur mustard, Di-2-chloroethyl sulfide, Agent hd, Kampstoff “lost”, Agent THD, 2,2′-Dichloroethyl sulfide, Gelbkreuz [Czech], Sulphur mustard gas, Sulfide, bis(2-chloroethyl), 2,2′-Dichlorodiethyl sulfide, UNII-T8KEC9FH9P, Di-2-chloroethyl sulphide, Bis(2-chloroethyl)sulphide, Bis(beta-chloroethyl)sulfide, Bis(2-chloroethyl) sulphide, Bis(beta-chloroethyl)sulphide, 2,2′-Dichloroethyl sulphide, CCRIS 570, 2,2′-Dichlorodiethyl sulphide, HSDB 336, beta,beta’-Dichloroethyl sulfide, beta,beta-Dichlor-ethyl-sulphide, CHEBI:25434, beta,beta’-Dichloroethyl sulphide, BIS(2-CHLOROETHYL)SULFIDE, Diethyl sulfide, 2,2′-dichloro, Dichloroethyl sulfide [Forbidden], QKSKPIVNLNLAAV-UHFFFAOYSA-N, Ethane, 1,1′-thiobis(2-chloro-, Ethane, 1,1′-thiobis[2-chloro-, HD, BRN 1733595, 1-Chloro-2-(beta-chloroethylthio)ethane, Bis-(2-chloroethyl) Sulfide, Mustardgas, Psoriazin, KampfstoffLost, Bis(beta-chloroethyl) sulfide, Yellow Cross, Yellow Cro ss, S Lost, Mustard T- mixture, Dichloroethyl sulfide, Ethane, 1,1′-thiobis(2-chloro)-, 2-chloroethylsulphide, Kampfstoff ”lost”, bis(2-chloroethyl)sulfane, C4H8Cl2S, T8KEC9FH9P, Di(2-chloroethyl) sulfide, bis-(2-chloroethyl)sulfide, AC1L1V8Y, HD (chemical warfare agent), SCHEMBL43809, CHEMBL455341, Bis(.beta.-chloroethyl) sulfide, CTK4J2795, beta, beta’-dichloroethyl sulfide, beta,beta’-dichlorodiethyl sulfide, Ethane,1,1′-thiobis[2-chloro-, .beta.-Chloroethylisobutyl sulfide, beta, beta’-dichlorodiethyl sulfide, .beta.,.beta.-Dichloroethyl sulfide, 1,1′-sulfanediylbis(2-chloroethane), .beta.,.beta.’-Dichloroethyl sulfide, 1-chloro-2-(2-chloroethylthio)ethane, AKOS006275641, 1-chloro-2-[(2-chloroethyl)thio]ethane, 1-chloro-2-(2-chloroethylsulfanyl)ethane, 1-Chloro-2-(.beta.-chloroethylthio)ethane, LS-147886, 1-chloranyl-2-(2-chloroethylsulfanyl)ethane, 1-Chloro-2-[(2-chloroethyl)sulfanyl]ethane, 1-Chloro-2-[(2-chloroethyl)sulfanyl]ethane #, C19164, 92373-EP2280008A2, 92373-EP2284157A1, 92373-EP2287163A1, 92373-EP2298747A1, 92373-EP2305257A1, 92373-EP2305678A1, MUSTARD GAS [BIS-2-CHLOROETHYL SULFIDE], A828174, 172672-70-7, 39472-40-7, 68157-62-0, 69020-37-7

Removed Synonyms

Gas, Mustard, Sulfide, Dichlorodiethyl, Di 2 chloroethyl Sulfide, Sulfide, Di-2-chloroethyl, CID10461, UN 2927, 4-01-00-01407 (Beilstein Handbook Reference), D009151, THD, HS, SM

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