Bis(2-chloroethyl)ether
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Bis(chloroethyl) ether is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula O(CH2CH2Cl)2. It is an
ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R†...
with two 2-chloroethyl substituents. It is a colorless liquid with the odor of a
chlorinated In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. ...
solvent.


Reactions and applications

Bis(chloroethyl) ether is less reactive than the corresponding
sulfur mustard Mustard gas or sulfur mustard are names commonly used for the organosulfur chemical compound bis(2-chloroethyl) sulfide, which has the chemical structure S(CH2CH2Cl)2, as well as other species. In the wider sense, compounds with the substituen ...
S(CH2CH2Cl)2. In the presence of base, it reacts with
catechol Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It ...
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 Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. It is also an important pheromone in certain s ...
and two molar equivalents of sodamide in a ring-forming reaction. When treated with strong base, it gives
divinyl ether Divinyl ether is the organic compound with the formula . It is a colorless, volatile liquid that has mainly been of interest as an inhalation anesthetic. It is prepared by treating bis(chloroethyl) ether with base. History The analytical te ...
, 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.


See also

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Bis(chloromethyl) ether Bis(chloromethyl) ether is an organic compound with the chemical formula (ClCH2)2O. It is a colourless liquid with an unpleasant suffocating odour and it is one of the chloroalkyl ethers. Bis(chloromethyl) ether was once produced on a large scale ...
*
Sulfur mustard Mustard gas or sulfur mustard are names commonly used for the organosulfur chemical compound bis(2-chloroethyl) sulfide, which has the chemical structure S(CH2CH2Cl)2, as well as other species. In the wider sense, compounds with the substituen ...


References

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