Bis(2-chloroethyl)selenide

Selenium mustard
Names
	Preferred IUPAC name 1-Chloro-2-[(2-chloroethyl)selanyl]ethane
Identifiers
CAS Number	4730-83-0;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL288408;
ChemSpider	23134672;
PubChem CID	14699165;
	InChI InChI=1S/C4H8Cl2Se/c5-1-3-7-4-2-6/h1-4H2 Key: FFMUKNDYULFLJK-UHFFFAOYSA-N;
	SMILES C(C[Se]CCCl)Cl;
Properties
Chemical formula	C4H8Cl2Se
Molar mass	205.98 g·mol−1
Appearance	low-melting colorless solid
Melting point	24 °C (75 °F; 297 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bis(2-chloroethyl)selenide is the organoselenium compound with the formula 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.^[1]^[2]^[3]^[4]^[5]

References

^ Kang SI, Spears CP (April 1987). "Linear free energy relationships and cytotoxicities of para-substituted 2-haloethyl aryl selenides and bis(2-chloroethyl) selenides". Journal of Medicinal Chemistry. 30 (4): 597–602. doi:10.1021/jm00387a003. PMID 3560155.
^ Kang SI, Spears CP (June 1990). "Phenyl selenones: alkyl transfer by selenium-carbon bond cleavage". Journal of Medicinal Chemistry. 33 (6): 1544–7. doi:10.1021/jm00168a003. PMID 2342050.
^ Kang SI, Spears CP (January 1990). "Structure-activity studies on organoselenium alkylating agents". Journal of Pharmaceutical Sciences. 79 (1): 57–62. doi:10.1002/jps.2600790114. PMID 2313578.
^ Hu X, Tian Z, Chen Y, Lu X (2000). "One-Pot Two-Step Approach to Selenides. Phase-Transfer Catalyzed Synthesis of ω-Hydroxyalkyl Selenides". Synthetic Communications. 30 (3): 523–529. doi:10.1080/00397910008087348. S2CID 94951635.
^ Potapov VA, Kurkutov EO, Musalov MV, Amosova SV (February 2014). "Synthesis of bis(2-haloethyl) selenides by reaction of selenium dihalides with ethylene". Russian Journal of Organic Chemistry. 50 (2): 291–292. doi:10.1134/S1070428014020250. S2CID 97109063.

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