{{Chembox | Name = Selenium mustard | ImageFile = Selenium-mustard_structure.png | ImageClass = skin-invert-image | ImageSize = 250px | PIN = 1-Chloro-2-[(2-chloroethyl)selanyl]ethane | Section1 = {{Chembox Identifiers | CASNo = 4730-83-0 | ChemSpiderID = 23134672 | PubChem = 14699165 | SMILES = C(C[Se]CCCl)Cl | ChEMBL = 288408 | StdInChI = 1S/C4H8Cl2Se/c5-1-3-7-4-2-6/h1-4H2 | StdInChIKey = FFMUKNDYULFLJK-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | C=4|H=8|Cl=2|Se=1 | Appearance = low-melting colorless solid | MeltingPtC = 24 }} | Section3 = {{Chembox Hazards | LD50 = }} }}
'''Bis(2-chloroethyl)selenide''' is the organoselenium compound with the formula {{chem2|Se(CH2CH2Cl)2}}. As a haloalkyl derivative of selenium, it is an analogue of bis(2-chloroethyl)sulfide, the prototypical sulfur mustard used in chemical warfare. Bis(2-chloroethyl)selenide has not been used as a chemical warfare agent, however it is still a potent alkylating agent and has potential in chemotherapy.<ref>{{cite journal | vauthors = Kang SI, Spears CP | title = Linear free energy relationships and cytotoxicities of para-substituted 2-haloethyl aryl selenides and bis(2-chloroethyl) selenides | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 4 | pages = 597–602 | date = April 1987 | pmid = 3560155 | doi = 10.1021/jm00387a003 }}</ref><ref>{{cite journal | vauthors = Kang SI, Spears CP | title = Phenyl selenones: alkyl transfer by selenium-carbon bond cleavage | journal = Journal of Medicinal Chemistry | volume = 33 | issue = 6 | pages = 1544–7 | date = June 1990 | pmid = 2342050 | doi = 10.1021/jm00168a003 }}</ref><ref>{{cite journal | vauthors = Kang SI, Spears CP | title = Structure-activity studies on organoselenium alkylating agents | journal = Journal of Pharmaceutical Sciences | volume = 79 | issue = 1 | pages = 57–62 | date = January 1990 | pmid = 2313578 | doi = 10.1002/jps.2600790114 }}</ref><ref>{{cite journal | vauthors = Hu X, Tian Z, Chen Y, Lu X | title = One-Pot Two-Step Approach to Selenides. Phase-Transfer Catalyzed Synthesis of ω-Hydroxyalkyl Selenides. | journal = Synthetic Communications | date = 2000 | volume = 30 | issue = 3 | pages = 523–529 | doi = 10.1080/00397910008087348 | s2cid = 94951635 }}</ref><ref>{{cite journal | vauthors = Potapov VA, Kurkutov EO, Musalov MV, Amosova SV | title = Synthesis of bis(2-haloethyl) selenides by reaction of selenium dihalides with ethylene. | journal = Russian Journal of Organic Chemistry | date = February 2014 | volume = 50 | issue = 2 | pages = 291–292 | doi= 10.1134/S1070428014020250| s2cid = 97109063 }}</ref>
==See also== * Diethyl selenide * O-Mustard
==References== {{reflist}}
Category:Alkylating agents Category:Chloroethyl compounds Category:Mustard compounds Category:Selenoethers
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