Chlorovinyl arsines

Chlorovinyl arsines chlorovinyl dichloroarsine, dichlorovinyl chloroarsine and trichlorovinyl arsine and mixtures of these qv. It is interesting that several authors refer to the many varieties of lewisite. The chlorovinyl dichloroarsine variant qv is said to be typical. 

Arsine, (2-chlorovinyl) dichloro-Arsonous dichloride, (2-chloroethenyl)... 

Dot Marking Toxic liquids, n.o.s. Dichloro-(2-chlorovinyl)arsine UN 2810 Dot Placard Poison... 

Dichloro (2-chlorovinyl) arsine C1CH = CHAsC12 7.1 times heavier than air None... 

Other organoarsenicals, most notably lewisite (dichloro[2-chlorovinyl]arsine), were developed in the early twentieth century as chemical warfare agents. Arsenic trioxide was reintroduced into the United States Pharmacopeia in 2000 as an orphan drug for the treatment of relapsed acute promyelocytic leukemia and is finding expanded use in experimental cancer treatment protocols (see Chapter 54). Melarsoprol, another trivalent arsenical, is used in the treatment of advanced African trypanosomiasis (see Chapter 52). 

Several vinylidene complexes of the group VI metals have been obtained by heating n-chlorovinyl derivatives with tertiary phosphines, phosphites, arsines, or stibines (9, 30) ... 

Bis(2-chloroethylthio)pentane Bis(2-chloroethylthiomethyl)ether Bis(2-chloroethylthioethyl)ether 2-Chlorovinyldichloroarsine Bis(2-chlorovinyl)chloroarsine Tris(2-chlorovinyl)arsine Bis(2-chloroethyl)ethylamine Bis(2-chloroethyl)methylamine Tris(2-chloroethyl)amine... 

Lewisite [dichloro(2-chlorovinyl)arsine] is an organic arsenical known for its vesicant properties (Rosenblatt et al., 1975). It has a molecular weight of 207.32, vapor pressure of 0.58 mm HG at 25°C, a liquid density of 1,89 g/cm at 25°C, freezing point of -18°C, boiling point of 190°C, and is negligibly soluble in water (DA, 1974). The chemical structure of lewisite is shown below. Lewisite may occur as a trans-isomer and as a cis-isomer. In aqueous solutions, the cis-isomer undergoes photoconversion to the trans-isomer (Clark, 1989). hi the presence of moisture, lewisite is rapidly converted to the more stable but highly toxic lewisite oxide (2-chlorovinylarsenous acid) (Cameron et al., 1946). 

Lewisite [L or L-1 dichloro(2-chlorovinyl) arsine] is an arsenical vesicant developed early in the 20th century. Lewisite occurs as cis- and tranx-isomers the typical ratio being 10 90. Several impiuities including 6w(2-chlorovinyl) chloroarsine (L-2) and tnY(2-chlorovinyl)arsine (L-3) are typically present. The chemical and physical properties of the cis- and tranj-isomers are similar. 

Lewisite (L) Synonyms 2-chlorovinyldichloroarsine (2-chlorovinyl)arsenous dichloride beta-chlorovinyldichloroarsine dichloro(2-chlorovinyl) arsine chlorovinylarsine dichloride EA 1034... 

Inns, R.H., Rice, P. (1993). Efficacy of dimercapto chelating agents for the treatment of poisoning hy percutaneously applied dichloro(2-chlorovinyl)arsine in rabbits. Hum. Exp. Toxicol. 12 241-6. 

SYNS (2-CHLOROETHENYL) ARSONOUS DICHLORIDE P-CHLOROVINYLBICHLOROARSINE 2-CHLOROVINYLDICHLOROARSINE (2-CHLOROVINYL)DICHLOROARSINE DICHLORO(2-CHLOROVINYL)ARSINE n LE STSITE n LEWISITE (ARSENIC COMPOUND)... 

SYNS ARSINE, CHLORO(2-CHLOROVINYL)PHENYL- PHENYL(P-CHLOROVINYL)CHLORARSINE TL 59... 

In general, arsenical compounds have an aggressive action when two of the three valences of the arsenic atom are linked to like atoms or groups and the third to a different atom or radicle. If all the three valences of the arsenic atom are linked to similar atoms or radicles the compound has practically no aggressive action. Thus in the series of chlorovinyl arsines, it has been found that trichlorovinyl arsine has practically no aggressive action compared with chlorovinylchloroarsine or dichlorovinyl chloroarsine ... 

It combines with hydrogen under the influence of light and heat, and reacts energetically with most of the non-metals forming the respective chlorides. By this method arsenic trichloride may be prepared and this is employed in the preparation of the chlorovinyl arsines (Perkins s method) and diphenyl chloroarsine (Michaelis s method). Sulphur chloride is prepared similarly, and this is employed in the preparation of dichloroethyl sulphide by Guthrie s method. 

Methyl dichloroarsine. Ethyl dichloroarsine. Chlorovinyl arsines. Phenyl dichloroarsine. Diphenyl chloroarsine. Diphenyl cyanoarsine. 

Most of the aliphatic and aromatic arsines employed during the war of 1914-18 were substances which had been known for some time. The only new substances are the chlorovinyl arsines and phenarsazine chloride, of whose practical efficiency somewhat conflicting opinions are still held. 

Even the chlorovinyl arsines, although they are easily prepared, do not seem to be sufficiently aggressive in their action to replace the aromatic arsines. According to several authorities, experiments on the methods of military application of the chlorovinyl arsines have been abandoned even in America. 

In this mixture trichlorovinyl arsine always predominates and this substance has only a minor interest as a war gas, for its toxicity is low. Chlorovinyl dichloroarsine, which, besides its irritant action on the respiratory passages, also has a vesicant action similar to that of dichloroethyl sulphide, is of much greater importance. The resemblance in the properties of these two substances has been attributed to the presence of the two similar groups ... 

Later, various other compounds were prepared and examined for possible emplo5nnent as war gases. These are similar in constitution to the chlorovinyl arsines and are prepared similarly jS Bromovinyl dibromoarsine (b.p. 140° to 143° C. at 16 mm. mercury pressure) was prepared by Lewis and Stiegler by the action of acetylene on arsenic bromide mixed with aluminium chloride ... 

All these compounds, like the chlorovinyl arsines, are oily substances, somewhat yellow in colour, with extremely unpleasant odours. Their aggressive properties are still rather indefinite with the exception of /3 chlorovinyl methyl chloroarsine, which does not irritate the nasal tissues like the chlorovinyl arsines, but produces blisters on the skin which heal only with difficulty. 

The mixture of the three chlorovinyl arsines is obtained, as indicated above, by the action of acetylene on arsenic trichloride. 

In the laboratory, the preparation of the chlorovinyl arsines may be carried out by condensing arsenic trichloride with... 

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