Bis(chloroethyl) ether explained

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.^[1]

Reactions and applications

Bis(chloroethyl) ether is less reactive than the corresponding sulfur mustard S(CH₂CH₂Cl)₂.^[1] In the presence of base, it reacts with catechol to form dibenzo-18-crown-6:

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:

O(CH₂CH₂Cl)₂ + 2 KOH → O(CH=CH₂)₂ + 2 KCl + 2 H₂O

Toxicity

The is 74 mg/kg (oral, rat).^[1] Bis(chloroethyl) ether is considered as a potential carcinogen.^[2]

See also

• Bis(chloromethyl) ether
• Sulfur mustard

Notes and References

1. Wang. Q. Q.. Begum. R. A.. Day. V. W.. Bowman-James. K.. Kristin Bowman-James. 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. 10.1039/c2ob26482j. 23070251. 9721325.
2. Web site: CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): Dichloroethyl ether - NIOSH Publications and Products. 2017-11-07. www.cdc.gov. en-us. 2018-10-31.