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Bis(chloroethyl) ether

Dangerous for the environment (N) Vesicant | NFPA-H = 4 | NFPA-F = 1 | NFPA-R = 1 152 ppm (mouse, 2 hr) 500 ppm (guinea pig, 1 hr) 500 ppm (guinea pig, 5 hr) Nitrogen mustard 2-Bromoethyl ether

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.

Reactions and applications

Bis(chloroethyl) ether is less reactive than the corresponding sulfur mustard S(CH2CH2Cl)2.

:[[File:Synthesis of dibenzo-18-crown-6.png|450px]]

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).

References

References

  1. {{PGCH. 0196
  2. {{IDLH. 111444. Dichloroethyl ether
  3. (2012). "Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity Wang, Qi-Qiang; Begum, Rowshan Ara; Day, Victor W.; Bowman-James, Kristin". Organic & Biomolecular Chemistry.
  4. Pedersen, C. J.. (1972). "Macrocyclic Polyethers: Dibenzo-18-Crown-6 Polyether and Dicyclohexyl-18-Crown-6 Polyether".
  5. (2000). "Anesthetics, General".
Wikipedia Source

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ethers alkylating-agents iarc-group-3-carcinogens chloroethyl-compounds
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