Dichlorodiethyl sulfide

Kinetic studies of various systems have been carried out as follows the reaction of 2,2 -dichlorodiethyl sulfide and of 2-chloroethyl ethyl sulfide with diethylenetriamine and triethylamine in 2-methoxyethanol ° the catalysed reactions of substituted phenols with epichlorohydrin the reactions of para-substituted benzyl bromides with isoquinoline under high pressure the reactions of O-alkylisoureas with OH-acidic compounds [the actual system was N, N -dicyclohexyl-0-(l-methylheptyl)isourea with acetic acid] and tlie ring opening of isatin in aqueous binary mixtures of methanol and acetonitrile cosol vents. 

Sulfur mustard 2,2 -Dichlorodiethyl sulfide Mustard gas, Kampfstoff, Yperite,... 

Chlorinated Ethers. Ethylene chlorohydrin reacts with sulfuric acid to form f./T-dichloroethyl ether. It is u byproduct of ethylene glycol production. The chlorines on this ether are inert, making it a good solvent. Further chlorination at 20-30 C gives diethyl ether which hydrolyzes to chloroacclaldehyde and ethylene chlorohydrin. Ethylene and sulfur monochloride react to give /J./i -dichlorodiethyl sulfide (mustard gas), which Is a thioelher. 

PM3 and SM3-PM3 semiempirical MO study of die conventional S 2 hydrolysis and neighbouring-group hydrolysis reaction mechanisms in die gas phase and in aqueous solution for 2,2,-dichlorodiethyl sulfide has been described.93 The calculations predict substantially faster reactions in aqueous solution, with the neighbouring-group mechanism always being preferred. Various other details of the mechanisms were elucidated. 

Mustard Gas Brit desgn for dichlorodiethyl-sulfide (CWA) (See also Yperite)... 

Dehydrochlorination of /i,/f-dichlorodiethyl sulfide promoted by PhCH2NR3+ and KOH or NaOH in aqueous heptane mixtures has been found to give (CH2=CH)2S via CH2=CHSCH2CH2C1 under phase-transfer and single-phase conditions.14... 

E.R.J. Wils and A.G. Hulst, Mass spectra of some derivatives of 2,2 -dichlorodiethyl sulfide (Mustard Gas), Fresenius Z. Anal. Chem., 331, 471-474 (1985). 

S.D. Christesen, Vibrational spectra and assignments of diethyl sulfide, 2-chlorodiethyl sulfide and 2,2/-dichlorodiethyl sulfide, J. Raman Spec-trosc., 22, 459-465 (1991). 

Meier, H., Gross, C., Papirmeister, B. (1987). 2,2 -dichlorodiethyl sulfide (sulfur mustard) decreases NAD levels in human leukocytes. Toxicol. Lett. 39 109-22. 

Bartlett, P.D., Swain, C.G. (1949). Kinetics of hydrolysis and displacement reactions of P,P -dichlorodiethyl sulfide (mustard gas) and of P-chloro-P -hydroxydiethyl sulfide (mustard chlo-rohydrin). J. Am. Chem. Soc. 71 1406-15. 

Janouchek, B., Horakova, M., Bartak, P. (1987). Treatment of psoriasis with dichlorodiethyl sulfide. Phlebologie 40 171-5. 

Meier, H.L., Johnson, J.B. (1992). The determination and prevention of cytotoxic effects induced in human lymphocytes by the alkylating agent 2,2 -dichlorodiethyl sulfide (sulfur mustard, HD). Toxicol. Appl. Pharmacol. 113 234-9. 

SYNS BIS(P-CHLOROETHYL)SULFIDE BIS(2-CHLOROETHYL)SULPHIDE l-CHLORO-2-(p-CHLOROETHYLTHIO)ETHANE P.P-DICHLOR-ETHYDSULPHIDE D 2,2 -DICHLORODIETHYL SULFIDE DI-2-CHLOROETHYL SULFIDE D P,P -DICHLOROETHYL SULFIDE 2,2 -DICHLOROETHYL SULPHIDE (MAK) DISTILLED MUSTARD KAMPSTOFF LOST MUSTARD GAS MUSTARD HD MUSTARD VAPOR SCHWEFEL-LOST S-LOST S MUSTARD SULFUR MUSTARD SULFUR MUSTARD GAS SULPHUR MUSTARD GAS 1,1 -TH10BIS(2-CHLOROETHANE) YELLOW CROSS LIQUID YPERITE... 

P,P -DICHLORODIETHYL-N-METHYLAMINE HYDROCHLORIDE see BIE500 DICHLORODIETHYLSILANE see DEY800 DICHLORODIETHYLSTANNANE see DEZOOO 2,2 -DICHLORODIETHYL SULFIDE see BIH250 DICHLORODIETHYLTIN see DEZOOO... 

Reports of quaternization at the already substituted nitrogen should be viewed with suspicion, and one of the products of the reaction of imidazole with 2,2-dichlorodiethyl sulfide (mustard gas) designated as (55) is more likely to be (56) or (57). The observations of Pinner and Schwarz in 1902 that the quaternary salt obtained from 1-methylimidazole and 1-bromopentane could be decomposed by alkali to give both aminomethane and 1-aminopentane was the first piece of evidence (more recently confirmed by NMR studies) to support the accepted view that quaternization takes place at the unsubstituted ring nitrogen. 

Synonyms Sulfur mustard l,l-Thiobis(2-chloro-ethane) l-Chloro-2-(/l-chloroethylthio)ethane 2,2 -Dichlorodiethyl sulfide Distilled mustard S mustard S-lost SchwefeTlost Yellow cross liquid Yperite Kampstoff lost HD HT H... 

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