Mustard, Bis

Mustard and Related Vesicants. Mustard, bis(2-chloroethyl) sulfide [505-60-2] (Chemical Agent Symbol HD), C1(CH2)2S(CH2)2C1, is a colodess, oily hquid when pure. Most samples have a characteristic garliclike odor. It is primarily a vesicant bUsters are formed by either Hquid or vapor contact. Mustard also attacks the eyes and lungs and is a systemic poison, so that protection of the entire body must be provided. It is insidious in its action there is no pain at the time of exposure, and symptoms usually do not appear until several hours after exposure. 

MUSTARD Bis(2-chloroethyl) sulfide Vesicant — Chemical Blister Agent 100 mg/ Kg (skin) 1500 mg-min/M3 (air) A blister agent which causes painfiil bhst-ers, and attacks the mucous membranes. 

Synonyms Sulfur mustard bis-2-chloroethyl sulfide di-2-chloroethyl sulfide l,l-thiobis(2-chloroethane) chemical agent symbol HD... 

As part of a study to identify the degradation products of sulfur mustard, bis(2-chloroethyl) sulfide, the behavior of various sulfonium salts towards electrospray ionization mass spectrometry has been investigated. Among the compounds studied was 3 -(2-chloroethyl)pentamethylene sulfonium tetrafluoroborate. The ion was readily detected at the 0.01 M level with no ion fragmentation <1997JMP1247>. 

The final type of chemical toxicity that will be presented are the vesicants, chemicals that cause blisters on the skin. There are two classes of blisters that implicate different mechanisms of vesication. Intraepidermal blisters are usually formed due to the loss of intercellular attachment caused by cytotoxicity or cell death. The second class occurs within the epidermal-dermal junction (EDJ) due to chemical-induced defects in the basement membrane components. The classic chemical associated with EDJ blisters is the chemical warfare agent sulfur mustard (bis-2-chloroethyl sulfide HD). HD is a bifunctional alkylating agent that is highly reactive with many biological macromolecules, especially those containing nucleophilic groups such as DNA and proteins. 

FIGURE 41.1. Chemical stmcture of sulfur mustard [bis(2-chloroethyl) sulfide]. 

Osborne MR, Wilman DE and Lawley PD (1995). Alkylation of DNA by the nitrogen mustard bis(2-chloroethyl)methylamine. Chem Res Toxicol, 8, 316-320. 

Bulk agents included mustard (bis-2-chloroethyl sulfide, 12 tonnes), lewisite (2-chlorovinyl-dichloro arsine, 2.5 tonnes) and nerve agents in the G- and V-classes (0.3 tonne). The scrap (400 tonnes) consisted mainly of several thousand empty, mustard-contaminated 210 drums and ordnance casings stored in open pits. All of the lewisite and some of the mustard and nerve agents were stored in 1 ton containers. Nerve agents were also stored in non-explosive ordnance, primarily 105 and 155 mm artillery shells. Mustard which had aged or had been thickened with polymers was also contained in non-explosive ordnance. The waste previously had been sorted by type, collected and stored at four remote, protected sites on the EPG. 

Almost all proliferant states since World War I have manufactured vesicants, principally sulfur mustard, bis(2-chloroethyl) sulfide. There are several routes to this compound, none of which require sophisticated technology and/or special materials Virtually all those producing mustard have experienced a large number of industrial accidents resulting in casualties from mustard burns. Nitrogen mustards have been synthesized only in pilot plant quantities, but did not require any unusual processes or materials. Lewisite was produced by both the United States and the Soviet Union during World War II. The plants were quite small and unsophisticated by today s standards. Lewisite is an arsenical and as such would require unusually large amounts of arsenates in its production. 

Included in this category of chemical agents are various forms of "mustard," an arsenical compound called Lewisite, and phosgene oxime. No evidence suggests that Lewisite or phosgene oxime has ever been used on the battlefield, but sulfur mustard bis [2-chloroethyl] sulfide) has been used in several wars, most recently in the Iran-Iraq conflict, and it is considered the most likely to be used on the battlefield. An immediate precursor, thioglycol, has many industrial uses and is available commercially. A simple substitution reaction yields mustard. Sidell et al. (1997) is the primary source of the information presented in this section. 

Nitrogen mustards bis(2-Chloroethyl) ethylamine HNl CHjCHzCI CHjCHz N GHjCHiCI Ethyldiethanolamine EDEA CH2CH2OH CHsCHz N CHzCHzOH... 

Write a mechanism for the hydrolysis of the nitrogen mustard bis(2-chloroethyl) methylamine. 

Bis(2-chloroethylthio)-n-pentane Bis(2-chloroethylthiomethyl)ether O-Mustard Bis(2-ohloroethylthioethyl)ether... 

Biotin Ultra IV ((Bis 3-aminopropyl)amine) see 3,3 -Iminobis(propylamine) (l,3-Bis(2-chloroethyl)nitrosourea) see Carmustin (Bis(2-chloroethyl)sulfide) see Sulfur mustard (Bis(2-ethylhexyl)adipate) see Di-(2-ethylhexyl)adipate (Bis(2-ethylhexyl) phthalate) see Di-(2-ethylhexyl) phthalate (Bis-2-hydroxyethyl ether) see Diethylene glycol Xi... 

Sulfur mustard (Bis(2-chloroethyl)sulfide or CW Agent HD or Mustard gas) 505-60-2 Tx... 

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