3062. Dichloro(2-chlorovinyl)arsine

Nomenclature

CAS number: 541-25-3; 50361-05-2 ((E)-form) ; 34461-56-8 ((Z)-form)
As-(2-Chloroethenyl)arsonous dichloride; 2-chlorovinyldichloroarsine; chlorovinylarsine dichloride; Lewisite.
C2H2AsCl3; mol wt 207.32.
C 11.59%, H 0.97%, As 36.14%, Cl 51.30%.

Description and references

Vesicant used as chemical weapon. Prepn: S. J. Green, T. S. Price, J. Chem. Soc. 119, 448 (1921); W. L. Lewis, G. A. Perkins, Ind. Eng. Chem. 15, 290 (1923). Review of military experience: G. N. Jarman in Adv. Chem. Ser. 23, entitled “Metal-Organic Compounds,” M. Sittig, Ed. (ACS, Washington DC, 1959) pp 328-337. Determn of degradation products in soil: B. A. Tomkins et al., J. Chromatogr. A 909, 13 (2001); in urine: J. V. Wooten et al., J. Chromatogr. B 772, 147 (2002). Review of chemistry, toxicology and biological effects: M. Goldman, J. C. Dacre, Rev. Environ. Contam. Toxicol. 110, 75-115 (1989).

Chemical structure

Properties

Colorless, slightly oily liquid; darkens with time becoming violet-black or green. Faint odor of geranium. Vesicant. bp12.5 76-77°; bp26 93°; bp760 190°. d420 1.888. Sol in the common organic solvents. Insol in water, dil mineral acids. Absorbed by rubber, paint, varnish and porous materials. Rapidly hydrolyzed in aqueous medium. LD50 in rats (mg/kg): 50 orally; in rats, rabbits (mg/kg): 24, 6 dermally; 1, 2 s.c. (Goldman, Dacre).

Caution

Vapors are extremely toxic. Contact with skin may produce immediate, persistent stinging, followed by erythema and blistering; irritating to eyes; inhalation of 0.50 mg/l for 5 min is considered lethal in humans (Goldman, Dacre). Antidote: Dimercaprol, q.v.

Use

Chemical warfare agent.