The Chemistry of 1,1′-Thiobis-(2-Chloroethane) (Sulphur Mustard) Part I. Some Simple Derivatives

Development and validation of efficient stable isotope dilution LC–HESI–MS/MS method for the verification of β-lyase metabolites in human urine after sulfur mustard exposure

“…Reference chemicals of SBMSE and MSMTESE and the corresponding deuterated (d6) analogue of SBMSE were synthesized by the Finnish Institute for Verification of the Chemical Weapons Convention (VERIFIN, Department of Chemistry, University of Helsinki, Finland) according to previously published method [25]. Reference chemicals were determined to be >95% pure by 1 H NMR and LC-MS analysis (unpublished data).…”

Catalytic Processes for the Neutralization of Sulfur Mustard

“…The dehydrochlorinationr eactions of HDO and HDO 2 are exothermic and can be achieved upon reactionw ith aw eakb ase such as potassium carbonate. [43] In particular, the sulfone derivative can undergo dehydrochlorinationa tp hysio-logical pH to form divinylsulfone (DVSO 2 ;F igure 3), as trong Michael acceptorc apable of denaturating proteins faster than HD or HDO 2 . [46] For this reason, effective decontamination is only achieved when sulfur mustard is selectively oxidized to the non-vesicant sulfoxide.A st he kinetics of sulfideo xidation are higher than that of the sulfoxide, high selectivities can be anticipated.…”

“…In contrast, the doubly oxidized sulfone derivative ( HDO 2 ) is vesicant in much the same way as HD , and exhibits poor chemical stability with a hydrolysis rate and water solubility (6 g L −1 ) in between those of the sulfide and sulfoxide. The dehydrochlorination reactions of HDO and HDO 2 are exothermic and can be achieved upon reaction with a weak base such as potassium carbonate [43] . In particular, the sulfone derivative can undergo dehydrochlorination at physiological pH to form divinylsulfone ( DVSO 2 ; Figure 3), a strong Michael acceptor capable of denaturating proteins faster than HD or HDO 2 [46] .…”

“…This process leads to the initial formation of [2‐chloroethyl]vinylsulfide ( CEVS ), which can further evolve to divinylsulfide ( DVS ) by a second elimination reaction of HCl (Figure 2). For example, the reaction of HD and sodium ethoxide results in two back‐to‐back eliminations to form non‐vesicant DVS , which readily polymerizes [42–44] . The reaction of sulfur mustard with an aqueous base such as potassium hydroxide leads to a mixture of hydrolyzed and dehydrochlorinated products [45] .…”

Simultaneous determination of sulfur mustard and related oxidation products by isotope-dilution LC–MS/MS method coupled with a chemical conversion

“…The derivatization reagent, 2-(3,5-bis(mercaptomethyl)phenoxy) acetic acid (DSH) was synthesized in our laboratory according to a published method [20] and the purity was larger than 98%, which was determined by NMR (see Supplementary data). SMO and SMO 2 were home-synthesized [22] and their purity with more than 98% was checked by NMR and GC-MS (see Supplementary data). HPLC-grade acetonitrile was purchased from J&K Scientific LTD (China, Beijing).…”