Bis(chloroethyl) ether is an organic compound with the formula O(CH2CH2Cl)2. It is an ether with two 2-chloroethyl substituents. It is a colorless liquid with the odor of a chlorinated solvent.[3]
Reactions and applications
Bis(chloroethyl) ether is less reactive than the corresponding sulfur mustard S(CH2CH2Cl)2.[3] In the presence of base, it reacts with catechol to form dibenzo-18-crown-6:[4]
Bis(chloroethyl) ether can be used in the synthesis of the cough suppressant fedrilate. It is combined with benzyl cyanide and two molar equivalents of sodamide in a ring-forming reaction. When treated with strong base, it gives divinyl ether, an anesthetic:[5]
- O(CH2CH2Cl)2 + 2 KOH → O(CH=CH2)2 + 2 KCl + 2 H2O
Toxicity
The LD50 is 74 mg/kg (oral, rat).[3] Bis(chloroethyl) ether is considered as a potential carcinogen.[6]
See also
References
- ^ a b c d e f g h i j k NIOSH Pocket Guide to Chemical Hazards. "#0196". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Dichloroethyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c Wang, Q. Q.; Begum, R. A.; Day, V. W.; Bowman-James, K. (2012). "Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity Wang, Qi-Qiang; Begum, Rowshan Ara; Day, Victor W.; Bowman-James, Kristin". Organic & Biomolecular Chemistry. 10 (44): 8786–8793. doi:10.1039/c2ob26482j. PMID 23070251. S2CID 9721325.
- ^ Pedersen, C. J. (1972). "Macrocyclic Polyethers: Dibenzo-18-Crown-6 Polyether and Dicyclohexyl-18-Crown-6 Polyether". Organic Syntheses. 52: 66; Collected Volumes, vol. 6, p. 395.
- ^ Wollweber, Hartmund (2000). "Anesthetics, General". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_289. ISBN 978-3-527-30673-2.
- ^ "CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): Dichloroethyl ether - NIOSH Publications and Products". www.cdc.gov. 2017-11-07. Retrieved 2018-10-31.
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