Synthesis of halogen analogues of sulfur mustard

Abstract

Bis(2-chloroethyl) sulfide, known as mustard gas (HD), is a well-known, poisonous warfare agent whose first use on the battlefield dates back to the First World War. However, there are halogen analogues which, instead of two chlorine atoms bonded to carbon atoms in the beta position, have bromine, iodine, or fluorine atoms. These compounds were not used for military purposes and they were not covered by the Chemical Weapons Convention (CWC). Moreover, these are the substances that are very poorly described in the literature. However, due to their chemical structure and properties, they can be excellent imitators of sulfur mustard, used to carry out a number of tests without the need to use the above-mentioned chemical warfare agent. Halogen analogues of sulfur mustard can be used to study the course and kinetics of electrophilic and nucleophilic reactions, as well as to conduct the decontamination process, including its effectiveness, in much safer conditions, while maintaining the credibility of the results. The article reviews the literature data on the properties of halogen analogues of sulfur mustard and it presents descriptions of the synthesis of these compounds. Then, their analysis was carried out using gas chromatography coupled with an atomic emission detector (GC-AED) and gas chromatography with a mass spectrometer (GC-MS). As a result of the performed syntheses and analyses, it was possible to obtain the assumed chemicals and to collect their mass spectra, while the spectra of bis (2-iodoethyl) sulfide and bis (2-fluoroethyl) sulfide are not available in commercial mass libraries.