6316. Mustard Gas

Nomenclature

CAS number: 505-60-2
1,1′-Thiobis[2-chloroethane]; bis(2-chloroethyl)sulfide; β,β′-dichloroethyl sulfide; 2,2′-dichlorodiethyl sulfide; bis(β-chloroethyl)sulfide; 1-chloro-2-(β-chloroethylthio)ethane; sulfur mustard; yellow cross liquid; Kampfstoff “Lost”; Yperite.
C4H8Cl2S; mol wt 159.08.
C 30.20%, H 5.07%, Cl 44.57%, S 20.16%.

Description and references

War gas prepd by treating ethylene with sulfur chloride (Levinstein process): Mann, Pope, J. Chem. Soc. 121, 594 (1922); by treating β,β′-dihydroxyethyl sulfide with HCl gas (German process): Meyer, Ber. 19, 3260 (1886); Ann. 240, 310 (1887); Gomberg, J. Am. Chem. Soc. 41, 1427 (1919). Reactions and derivatives: Helfrich, Reid, ibid. 42, 1208 (1920). Toxicity: Anslow et al., J. Pharmacol. Exp. Ther. 93, 1 (1948). Review of carcinogenic risk: IARC Monographs 9, 181-192 (1975); of toxicology and human exposure: Toxicological Profile for Mustard Gas (PB2004-100006, 2003) 287 pp.

Chemical structure

Properties

Oily liquid. Deadly vesicant. Weak, sweet, agreeable odor. On cooling it forms prisms, mp 13-14°. d13 1.338 (solid); d420 1.2741 (liq). bp760 215-217°; bp10 98°. Volatile with steam. nD20 1.53125. Very sparingly sol in water; sol in fat solvents, other common organic solvents. High lipid soly. Vapor pressure: 0.025 mm (0°), 0.90 mm (30°). Hydrolyzed by alkalies. Recommended neutralizing agent and inactivator: Bleaching powder, sodium hypochlorite. LD50 in rats, mice (mg/kg): 3.3, 8.6 i.v. (Anslow).

Caution

Overexposure may cause severe irritation and tissue damage to eyes, skin, and respiratory and GI tracts; symptoms may be delayed in onset. This substance is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-176.

Use

Formerly in chemical warfare. In biological studies of alkylating agents.