Sulfure mustard

Properties. The physical properties of the mustards are summarized in Table 1. The sulfur mustards are only slightly soluble in water, whereas the nitrogen mustards are slightly soluble at neutral pH, but form water-soluble salts under acid conditions. Both sulfur and nitrogen mustards are extremely soluble in most organic solvents. 

With nitrogen mustards, the imonium ion, which apparendy forms even in the absence of any solvent, readily attacks another molecule to form a dimer. For this reason, the nitrogen mustards are less stable than sulfur mustards in long-term storage. 

The mustards readily alkylate inorganic thiosulfates to form Bunte salt anions (12,13). For sulfur mustard, the product is Cl(CH2)2S(CH2)2SSO 2-Phosphates react in a similar manner and the product isolated from sulfur mustard is Cl(CH2)2S(CH2)20PO 2. 

Sulfur mustard reacts rapidly with chlorine or with bleach, and this reaction is a suitable means of decontamination. Nitrogen mustards, however, chlorinate extremely slowly thus chlorination is not suitable for their decontamination. The formation of water-soluble salts, such as by neutralization with sodium bisulfate, is the usual method for nitrogen mustard removal from contaminated surfaces. The mustard salts are much less vesicant than the corresponding free bases. 

Nitrogen mustards such as 23 decompose to yield aziridinium ions 24 (Scheme 8.14). " As in the case of sulfur mustards, the reaction involves rate-limiting intramolecular displacement of p-chlorine by nitrogen. The resulting aziridinium ions... 

Chapter 1 Blister Agents DISTILLED SULFUR MUSTARD - HD... 

Solubility Soluble in sulfur mustards and chloropicrin insoluble in water soluble in ether, benzene, and acetone. 

Chapter One Blister Agents SULFUR MUSTARD MIXTURE - HT... 

Vesicants/blister agents sulfur mustard, lewisite, nitrogen mustard, mustard lewisite, and phosgene oxime. 

Skin erythema and blistering watery, swollen eyes upper airways sloughing with pulmonary edema metabolic failure neutropenia and sepsis (especially sulfur mustard, late in course). 

Lewisite, minutes Sulfur mustard, hours to days... 

Organic synthesis Sulfur mustard (HD) 1.18 Pharmaceuticals Sulfur dyes Insecticides Rubber vulcanization Polymerization catalyst Hardening of soft woods Extraction of gold from ores... 

Delayed-acting chemical Sulfur mustard Blistering, redness, swelling 2 to 24 hours... 

The interplay between the chemical and biological properties of the threat agent, on the one hand, and the specific attack scenario, on the other, can influence the lethality of the attack. Table 2-2 shows the relative respiratory toxicities (expressed as the lethal concentration of toxin at which 50 percent of test animals are killed, or LCT50, in milligrams per minute per cubic meter) of a variety of toxic gases compared with chlorine gas, which was used as a chemical weapon in World War I. According to Table 2-2, the nerve agent sarin (GB) has a respiratory toxicity approximately 100 times that of chlorine, while sulfur mustard (HD) is about 7 times more toxic. However, the lethality of an attack... 

Blister agents, which cause burns on the skin such as sulfur mustard gas, l,l -thiobis[2-chloroethane] (HD), and lewisite, (2-chloroethenyl) arsenous dichloride (L). 

Bi- and poly-thioethers with aliphatic backbones are produced by attack of RS on the appropriate haloalkane. This is the method of choice for RS(CH2)raSR (R = Me or Ph),26 MeC(CH2SR)3,27,28 MeS(CH2)raS(CH2)raSMe (n = 2 or 3) and MeS(CH2)raS(CH2) S(CH2) SMe.28,29 [Caution Some of these syntheses involve sulfur mustard derivatives as intermediates - these are very powerful vesicants and should be handled only with extreme care.] The other tridentates RS(CH2)3S(CH2)3SR (R = Et, Pr or Ph) may be obtained from nucleophilic attack by RS on the ditosylate TsO(CH2)3S(CH2)3OTs.30 Tetra-dentate thioethers involving o-phenylene interdonor linkages are also known.31 More recently the preparation and coordination chemistry of the silicon-apex derivative MeSi(CH2SMe)3 has been described.32... 

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