Gasson, E. J. published the artcileNew organic sulfur vesicants. IV. 1,2-Di(2-chloroethylthio)ethane and analogs, Quality Control of 1002-41-1, the publication is Journal of the Chemical Society (1948), 44-6, database is CAplus and MEDLINE.
1,2-Bis(2-hydroxypropylmercapto)ethane, b5 189-90°, m. 28°; the di-2-Cl analog b0.005 78-9°, m. 14-15°. HOC2H4SH with 30.5% H2O2 at a temperature below 50° gives bis(2-hydroxyethyl) disulfide, b0.015 106°, m. 25-6°. S(C2H4OH)2 and HOC2H4SH (100 g. total) in the ratio of 90:10, heated 75 min. at 90° with 400 cc. concentrated HCl, give 80.8% S(CH2CH2Cl)2 (I); a ratio of 80:20 gives 69% I and a ratio of 70:30 gives 54.6% I. An equimol. ratio (61:39) gives (from 106 g. reaction product) 46% I, 20.6 g. crude (CH2)2(SC2H4Cl)2, and some 1,17-dichloro-3,6,9,12,15-pentathiaheptadecane, Cl(C2H4S)5C2H4Cl, amorphous, m. 100°. The following (CH2)n(SC2H4X)2 were prepared by the method described in part II, using (CH2)nBr2 and HSC2H4OH with EtONa, followed by reaction with SOCl2; compounds with n = 0, 1, 3, and 4 were prepared to check the purity of previously reported compounds The empirical vesicant powers (V) are based on mustard gas= X=OH, X=Cl; B.p.,, mm., M.p.,, B.p.,, mm., M.p.,; n, °C., °C, °C., °C., V; 0, 106, 0.015, 25-6, 100, 0.5, -2 to 0, 1; 1, 114-15, 0.005, 18, 80-1, 0.03, 30.7, 200; 2, …, …, .., 140, 2, 57, 500; 3, 200, 4, 18, 86, 0.04, 11.5, 400-500; 4, 207, 3, 30, 104, 0.06 , -1, 400; 5, 210, 3, 30, 104, 0.003, -6, 200; 6, 130, 0.02, 45, 112, 0.03, 14-15, 50; 8, …, …, 60-1, .., …, 21-2, 1; 9, …, …, 63-4, .., …, 24, 1; 10, …, …, 70, .., …, 32, 1; 100.
Journal of the Chemical Society published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Quality Control of 1002-41-1.
Referemce:
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