Williams, A. H. published the artcileNew organic sulfur vesicants. II. Analogues of 2,2′-dichlorodiethyl sulfide and 2,2′-di(2-chloroethylthio)diethyl ether, Related Products of chlorides-buliding-blocks, the publication is Journal of the Chemical Society (1948), 38-42, database is CAplus and MEDLINE.
MeCH.CH2.O (680 g.), introduced at the rate of 0.7 cc./min., and H2S (throughput 45 l./h.) at 60° give 948 g. of product which yields 488 g. 2-hydroxy-1-propanethiol, b8 44.5-5°, n18D 1.4850, and 390 g. 2,2′-dihydroxydipropyl sulfide (I), b4 125°. ClCH2CHMeOH (b. 126-8°) and Na2S in EtOH, refluxed 10 min., give I. I (50 g.) in 200 cc. CHCl3, treated dropwise with 62 cc. SOCl2 and refluxed 30 min., gives bis(2-chloropropyl) sulfide, b10 105°, m. -40°. EtCHO (58 g.) in 300 cc. AcOEt at -5°, treated dropwise (3 h.) with 45 g. Br in 100 cc. AcOEt, and the mixture poured into 500 cc. absolute EtOH and kept 18 h. at room temperature, give CHMeBrCH(OEt)2, b13 67°; reaction with HSC2H4OH in EtONa-EtOH (refluxing 25 h.) gives α-(2-hydroxyethylmercapto)propionaldehyde di-Et acetal, b0.5 87°; hydrolysis of 40 g. with 200 cc. 3% HCl (24 h.) gives α-(2-hydroxyethylmercapto)propionaldehyde, an oil, reduction of which with (iso-PrO)3Al gives 2-hydroxyethyl 2-hydroxyisopropyl sulfide, b5 136-7°; SOCl2 yields 2-chloroethyl 2-chloroisopropyl sulfide, b7 88°, b12 105°, m. -24.5° (sulfilimine, m. 132°). S(CH2CH2SCH2CH2OH)2 (II) (C.A. 16, 409) and SOCl2 in CHCl3 (refluxed 30 min.) give 2,2′-bis(2-chloroethylmercapto)diethyl sulfide (III), m. 73-5° (chloroplatinate, mustard color, m. 136°; piperidide picrate, m. 180° (decomposition)). The Cl atom of III is removed by AgNO3 in boiling EtOH in 5 min. and by boiling H2O in 45 min. The following ethers were prepared from III and the appropriate phenol in EtOH-EtONa: diphenoxy, m. 59°; di-2-naphthoxy, m. 122°; bis(sym-tribromophenoxy), m. 107°; dieugenoxy, m. 86°; bis(phenylmercapto), m. 92-4°. III and NaI in MeOH, refluxed 10 min., give the bis(2-iodoethyl) analog, m. 102-3°; bis(2-thiocyanatoethyl) analog, m. 52°; the bis(2-cyanoethyl) analog could not be prepared, the reaction yielding (NCCH2CH2)2S and dithiane. II and PBr3 in CHCl3, refluxed 2 h., give the bis(2-bromoethyl) analog, b3.5 158-63.5° [bis(1-naphthylurethane), m. 150-2°]. (ClCH2CH2)2S2 b5 132-4° [bis(sym-tribromophenoxy) analog, m. 76°; dieugenoxy analog, m. 97°]. III in AcOH, treated with 6 mols. 30% H2O2 (1 h.) gives 2,2′-bis(2-chloroethylsulfonyl)diethyl sulfone, m. 174.5°; 2,2′-bis(2-hydroxyethylmercapto)diethyl sulfoxide, m. 57°; the sulfone m. 85-6°; the disulfide m. 79-81°; 2,2′-bis(2-chloroethylmercapto)diethyl sulfoxide, m. 63°; the sulfone m. 107-9°; 2,2′-bis(2-hydroxypropylmercapto)diethyl sulfide, m. 59°; di-2-Cl analog, m. 43.5°; 2,3-bis(2-hydroxyethylmercapto)-1,4-dioxane, oily [bis(1-naphthylurethane), m. 152°]; 2,3-bis(2-chloroethylmercapto)-1,4,-dioxane, b15 138-41°. 2-Hydroxyethyl 2-hydroxypropyl sulfide, b8 154°; 2-chloroethyl 2-chloropropyl sulfide, b4 88°, m. -23°. 2,2′-Bis(2-hydroxypropylmercapto)diethyl ether, b5 217-18°; di-2-Cl analog, b0.02 95-8°. 2,2′-Bis(2-hydroxyethymercapto)dipropyl sulfide, b1.5 240°; di-2-Cl analog. 2,2′-Bis(2-hydroxypropylmercapto)dipropyl sulfide, b0.5 210°; di-2-Cl analog, b0.02 108-9° (slight decomposition). If mustard gas is assigned an empirical vesicant power of 100, these compounds show values of 10 to 50.
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 C5H2ClF3N2, Related Products of chlorides-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Chloride,
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