Bis(chloroethyl) ether is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula O(CH₂CH₂Cl)₂. It is an

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

with two 2-chloroethyl substituents. It is a colorless liquid with the odor of a

chlorinated In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, ...

solvent.

Reactions and applications

Bis(chloroethyl) ether is less reactive than the corresponding

sulfur mustard Mustard gas or sulfur mustard is a chemical compound belonging to a family of cytotoxic and blister agents known as mustard agents. The name ''mustard gas'' is technically incorrect: the substance, when dispersed, is often not actually a gas, b ...

S(CH₂CH₂Cl)₂. In the presence of base, it reacts with catechol to form

dibenzo-18-crown-6 Dibenzo-18-crown-6 is the organic compound with the formula C6H4OCH2CH2OCH2CH2sub>2. It is a white solid that is soluble in organic solvents. As one of the most popular crown ethers, it facilitates the dissolution of many salts in organic solv ...

: :

Bis(chloroethyl) ether can be used in the synthesis of the cough suppressant

fedrilate Fedrilate is a centrally acting cough suppressant. It was patented as a mucolytic by UCB (company), UCB in 1971, but was never brought to market in the US. In the Netherlands, it has been marketed as Tussefan and in combination with guaifenesin a ...

. It is combined with benzyl cyanide and two molar equivalents of

sodamide Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the chemical formula, formula . It is a salt (chemistry), salt composed of the sodium cation and the azanide anion. This solid, which is dangero ...

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). Bis(chloroethyl) ether is considered as a potential carcinogen.

References

{{Reflist Ethers Organochlorides Alkylating agents IARC Group 3 carcinogens Chloroethyl compounds

Reactions and applications

Toxicity

See also

References