Thiosarin, sulfursarin or GBS, is the

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

analogous to

sarin Sarin (NATO designation GB G-series, "B"">Nerve_agent#G-series.html" ;"title="hort for Nerve agent#G-series">G-series, "B" is an extremely toxic synthetic organophosphorus compound.U.S. Chemical Warfare Policy: Hearings, Ninety-third Congress, Second Session. May 1, 2, 7, 9 and 14, 1974. pg 341-344 It differs structurally in that sulfur replaces the oxygen of the P=O bond. It is an extremely toxic substance related to G-agents.Ledgard, J. A Laboratory History of Chemical Warfare Agents. 171-174

Characteristics

For thiosarin, unlike sarin, the literature contains little information. It is reported as a colorless liquid with a characteristic organosulfur odor when pure. It is estimated to have a boiling point of 144-167 °C. It is a more nonpolar compound, with a solubility in water of 7 g/L. Thiosarin probably belongs to the IVA compound series, leaving it much less volatile than sarin. It has a greater persistence in the environment than sarin. Absorption frequencies of sarin derivatives showed that the frequency of stretching of the P-F and P=S bond of thiosarin is lower than that of its oxygenated analogue.

CW history and candidate

Its toxicity was discovered in the 1970s by Friedrick Wilhelm Hoffmann and Ray King Irino. They were responsible for synthesizing and analyzing a series of sulfur G-agent compounds.Hoffmann et al. US 4,012,465 The open literature reports that the compound has been cataloged as GS, but this statement is incorrect, it belongs to EA-1246. GS agents are a series of G compounds. GBS is generally lower than sarin. The little open military literature may be due to the low toxicity of this series of compounds. The possibility of a

chemical warfare Chemical warfare (CW) involves using the toxic properties of chemical substances as weapons. This type of warfare is distinct from nuclear warfare, biological warfare and radiological warfare, which together make up CBRN, the military a ...

agent candidate was raised when Bogomazov and his colleagues discovered that thiosarin had the ability to break through military gas mask filters, where it would then be converted to its analogue. An investigation by Vil Mirzayanov refuted these results. Thiosarin is used as a precursor to sarin.

Synthesis

The preparation route is quite similar to that of sarin. The synthesis routes of thiosarin are manifold. Regardless of the synthesis route chosen, the final reaction is usually the reaction of isopropyl methylthiophosphonochloridate with

fluorides Fluoride (). According to this source, is a possible pronunciation in British English. is an inorganic, monatomic anion of fluorine, with the chemical formula (also written ), whose salts are typically white or colorless. Fluoride salts ...

Reactions

Thiosarin has a tendency to convert to the all oxygen analogue by divers mechanisms.. In anhydrous medium, thiosarin is oxidized to form GB. Degradation of GBS

In the controlated aqueous medium, without the presence of oxygen, the tendency is to evolve

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The und ...

Sarin-S

Along with the discovery of the high toxicity of this series of compounds, Hoffmann discovered that the S-alkyl isomers, unlike the alkyl alkylphosphonothiol compounds, were less toxic than the G(S) agents.

References

{{Acetylcholine metabolism and transport modulators Nerve agents G-series nerve agents Acetylcholinesterase inhibitors Isopropyl esters Methylphosphonofluoridates Sulfur compounds