{"Abbreviation":["Sesquimustard","Agent Q","TL-86"],"Aliases":["Sesquimustard","Sesquimustard Q","Agent Q","Sesquisulfur Mustard","Bis(2-chloroethylthio)ethane","HSM 1","SM 1","1,8-Dichloro-3,6-dithiaoctane","3,6-Dithia-1,8-octanedichloride","TL 86","Sesqui-mustard Q","NSC 30025","Ethane, 1,2-bis(2-chloro-ethylthio)-","Ssm","NSC-30025","Ethane, 1,2-bis[(2-chloroethyl)thio]-","Ethane, 1,2-bis((2-chloroethyl)thio)-","1,2-Bis(β-chloroethylthio)ethane","Brn 1739199","Ethane, 1,2-bis(2-chloroethylmercapto)-","Sesqui-mustard","Ethane, 1,2-bis(2-chloroethylthio)-","Wln: g2s2s2g","Schembl384755","1,2-bis(chloroethylthio)ethane","HSDB 8400","NSC30025","Ethane,2-bis(2-chloro-ethylthio)-","Ethane,2-bis[(2-chloroethyl)thio-","Ethane,2-bis[(2-chloroethyl)thio]-","1,2-Bis[(2-chloroethyl)sulfanyl]ethane","Ethane,1,2-bis[(2-chloroethyl)thio]-","Ethane,2-bis[(2-chloroethyl)mercapto]-","DS-010843","1,2-Bis((2-chloroethyl)thio)ethane","Ethane, 1,2-bis((2-chloroethyl)mercapto)-","NS00120136","1-Chloro-2-((2-[(2-chloroethyl)sulfanyl]ethyl)sulfanyl)ethane #"],"Boiling Point":"Decomposes","CAS":"3563-36-8","ChemicalClasses":["thioether"],"Chirality":"achiral","Color/Form":"Solid","DTXSID":"7074793","Decomposition":"When heated to decomposition it emits very toxic fumes of SOx and Cl-.","Density":"1.27 at 25 °C g/cm\u003csup\u003e3\u003c/sup\u003e","Erowid Experience Reports":[],"Esters":[],"Formating":[],"HeavyAtomCount":10,"IUPACName":"1,2-bis(2-chloroethylsulfanyl)ethane","InChI":"InChI=1S/C6H12Cl2S2/c7-1-3-9-5-6-10-4-2-8/h1-6H2","InChIKey":"AMGNHZVUZWILSB-UHFFFAOYSA-N","MeSH Headers":[],"Melting Point":"56 °C","Metabolism/Metabolites":"Sesqui- and oxy-mustards pose a significant threat to military forces and civilians because they are potent vesicants. We have developed an isotope-dilution high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry method utilizing negative ion multiple reaction monitoring for the analysis of sesqui-mustard metabolites bis(2-hydroxyethylthio)alkanes (n = 1-5) and oxy-mustard metabolite bis(2-hydroxyethylthioethyl)ether in human urine. Relative standard deviations were \u003c 10% and the reportable limits of detection were 1 ng/mL in 0.5 mL of urine. We applied this method to 100 samples collected from individuals with no known exposure to sesqui- or oxy-mustards, and no urines showed detectable levels of any of the analytes, suggesting that these metabolites may be used for monitoring exposure to sesqui- and oxy-mustards.","MolecularFormula":"C\u003csub\u003e6\u003c/sub\u003eH\u003csub\u003e12\u003c/sub\u003eCl\u003csub\u003e2\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"219.2 g/mol","Non-Human Toxicity Values":"LC50 Mice inhalation 6 mg/cu m/10 min","Odor":"Garlic-like odor","Physical Description":"This is a chemical weapon related to sulfur mustard (mustard gas) and is expected to react in a similar fashion. See the chemical datasheet for sulfur mustard for more information.","PubChemId":19092,"PubChemTitle":"Sesquimustard","Records":{"UNII":{"Impurities":[]}},"Reddit Experience Reports":[],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Sesquimustard","Name":"1,2-Bis(2-chloroethylthio)ethane","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q50644964","Name":"1,2-Bis(2-chloroethylthio)ethane","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/19092","Name":"1,2-Bis(2-chloroethylthio)ethane","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=3563-36-8","Name":"1,2-Bis(2-chloroethylthio)ethane","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/5Y1NV229PO","Name":"1,2-Bis(2-chloroethylthio)ethane","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID7074793","Name":"1,2-Bis(2-chloroethylthio)ethane","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 19092, 1,2-Bis(2-chloroethylthio)ethane. Accessed August 24, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/19092\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/19092\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. 1,2-Bis(2-chloroethylthio)ethane. UNII: 5Y1NV229PO. Global Substance Registration System. Accessed August 24, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/5Y1NV229PO\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/5Y1NV229PO\u003c/a\u003e"],"SMILES":"C(CSCCCl)SCCCl","SaltData":[],"Salts":[],"Solubility":"Although sulfur mustards have limited solubility in water at neutral pH, the small quantity that dissolves is reactive.  /Sulfur mustards/","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 128.91 13.937\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#1ff01f\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h129v14H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m58.71 3.164 13.198 7.62M71.908 10.784l10.063-5.81M88.251 4.98l10.054 5.804M98.305 10.784l13.198-7.62M111.503 3.164l9.797 5.657M58.71 3.164 48.506 9.056M42.367 8.969 32.314 3.164M32.314 3.164l-13.199 7.62M19.115 10.784 7.609 4.142\" class=\"bond\"/\u003e\u003cpath fill=\"#c6c62c\" stroke=\"none\" d=\"M86.568.828v.661q-.387-.185-.732-.274-.34-.095-.655-.095-.554 0-.857.214-.298.214-.298.613 0 .327.196.5.203.167.756.274l.411.083q.756.143 1.113.506.364.363.364.971 0 .726-.489 1.101-.488.375-1.428.375-.352 0-.756-.083-.399-.078-.828-.232v-.697q.417.232.81.351.393.113.774.113.583 0 .893-.226.315-.226.315-.649 0-.369-.226-.577-.22-.209-.738-.31l-.411-.083q-.756-.149-1.095-.47-.34-.322-.34-.893 0-.667.465-1.048.47-.381 1.291-.381.352 0 .715.065.363.06.75.191\" class=\"atom\"/\u003e\u003cpath stroke=\"none\" d=\"M126.716 8.668v.715q-.339-.322-.726-.477-.387-.16-.822-.16-.857 0-1.315.523-.453.524-.453 1.518 0 .989.453 1.513.458.523 1.315.523.435 0 .822-.154.387-.161.726-.477v.703q-.357.244-.756.363-.393.119-.833.119-1.137 0-1.792-.69-.649-.697-.649-1.9 0-1.208.649-1.899.655-.696 1.792-.696.446 0 .839.119.399.119.75.357m1.02-.595h.614v5.209h-.614z\" class=\"atom\"/\u003e\u003cpath fill=\"#c6c62c\" stroke=\"none\" d=\"M46.973 8.448v.661q-.387-.185-.732-.274-.339-.095-.655-.095-.553 0-.857.214-.298.214-.298.613 0 .327.197.5.202.167.756.274l.411.083q.756.143 1.113.506.363.363.363.971 0 .726-.488 1.101t-1.429.375q-.351 0-.756-.083-.399-.078-.828-.232v-.697q.417.232.81.351.393.113.774.113.583 0 .893-.226.315-.226.315-.649 0-.369-.226-.577-.22-.209-.738-.31l-.411-.083q-.756-.149-1.095-.47-.339-.322-.339-.893 0-.667.464-1.048.47-.381 1.292-.381.351 0 .714.065.363.06.75.191\" class=\"atom\"/\u003e\u003cpath stroke=\"none\" d=\"M4.59 1.155v.715q-.339-.322-.726-.477-.387-.16-.822-.16-.857 0-1.315.524-.453.523-.453 1.518 0 .988.453 1.512.458.524 1.315.524.435 0 .822-.155.387-.161.726-.476v.702q-.357.244-.756.363-.393.119-.833.119-1.137 0-1.792-.69Q.56 4.477.56 3.275q0-1.209.649-1.899.655-.697 1.792-.697.446 0 .839.119.399.119.75.357M5.61.56h.614v5.209H5.61z\" class=\"atom\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"M81.971 4.974 76.94 7.879M88.251 4.98l5.027 2.902\" class=\"hi\"/\u003e\u003cpath stroke=\"#1ff01f\" d=\"m121.3 8.821-4.899-2.829\" class=\"hi\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m48.506 9.056 5.102-2.946M42.367 8.969 37.34 6.066\" class=\"hi\"/\u003e\u003cpath stroke=\"#1ff01f\" d=\"m7.609 4.142 5.753 3.321\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"1,2-Bis(2-chloroethylthio)ethane","UNII":"5Y1NV229PO","Wikidata":"Q50644964","Wikipedia":"Sesquimustard","XLogP":2.7}