Bis(chloroethyl) ether
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Through Organic compound and Ether
Reactions and applications
Bis(chloroethyl) ether is less reactive than the corresponding sulfur mustard S(CH2CH2Cl)2. 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
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Toxicity
The LD50 is 74 mg/kg (oral, rat). Bis(chloroethyl) ether is considered as a potential carcinogen.
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