Sesquimustard

Sesquimustard
Names
	Preferred IUPAC name 1,2-Bis[(2-chloroethyl)sulfanyl]ethane
	Other names Agent Q; TL-86; One-and-one-half mustard
Identifiers
CAS Number	3563-36-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	18025;
PubChem CID	19092;
UNII	5Y1NV229PO;
CompTox Dashboard (EPA)	DTXSID7074793 ;
	InChI InChI=1S/C6H12Cl2S2/c7-1-3-9-5-6-10-4-2-8/h1-6H2 Key: AMGNHZVUZWILSB-UHFFFAOYSA-N;
	SMILES C(CSCCCl)SCCCl;
Properties
Chemical formula	C6H12Cl2S2
Molar mass	219.18 g·mol−1
Appearance	white solid (impure samples: pale brown)
Melting point	56.5 °C (133.7 °F; 329.6 K)
Solubility in water	Insoluble, slowly degrades
Solubility	Alcohols, hydrocarbons, lipids, ethers, THF
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sesquimustard (military code Q) is the organosulfur compound with the formula (ClCH₂CH₂SCH₂)₂. Although it is a colorless solid, impure samples are often brown. The compound is a type of mustard gas, a vesicant used as a chemical weapon. From the chemical perspective, the compound is both a thioether and an alkyl chloride.

Because sesquimustard is a solid at room temperature, it is not as easily deployed as related liquid mustards. It was only ever deployed as mixtures with the original mustard, with phosgene, or as a solution. Since 1997, it has been listed under Schedule I of the Chemical Weapons Convention, as a substance with few uses outside of chemical warfare^[1]^[2]^[3] (although since then, it has been found to be useful in chemotherapy).^[4]

References

^ Vocci, Frank J.; Ballard, Thomas A.; Yevich, Paul; Punte, Charles L. (1963). "Inhalation toxicity studies with aerosols of sesqui-mustard". Toxicology and Applied Pharmacology. 5 (6): 677–684. doi:10.1016/0041-008X(63)90061-9. PMID 14082474. S2CID 2261517.
^ Gupta, A.K.; Dubey, D.K.; Kaushik, M.P. (2007). "A simple and economical chemical neutralization method for the destruction of sulfur mustard and its analogues". Journal of Hazardous Materials. 139 (1): 154–159. Bibcode:2007JHzM..139..154G. doi:10.1016/j.jhazmat.2006.06.016. PMID 16846683. S2CID 36625534.
^ Blum, Marc-Michael; Richter, Annika; Siegert, Markus; Thiermann, Horst; John, Harald (2020). "Adduct of the blistering warfare agent sesquimustard with human serum albumin and its mass spectrometric identification for biomedical verification of exposure". Analytical and Bioanalytical Chemistry. 412 (28): 7723–7737. doi:10.1007/s00216-020-02917-w. PMC 7550388. PMID 32902690. S2CID 221542205.
^ Smith, Susan L. (27 February 2017). "War! What is it good for? Mustard gas medicine". CMAJ. 189 (8): E321–E322. doi:10.1503/cmaj.161032. PMC 5325736. PMID 28246228.