Bis(chloromethyl) ether

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Bis(chloromethyl) ether
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Names
IUPAC name
bis(chloromethyl) ether
Other names
bis-CME, chloro-(chloromethoxy)methane, oxybis(chloromethane), bis-Chloromethyl ether, Chloromethyl ether, Dichlorodimethyl ether, Dichloromethyl ether
Identifiers
542-88-1
Abbreviations BCME
ChemSpider 21106500
EC Number 208-832-8
Jmol 3D model Interactive image
KEGG C19158 YesY
PubChem 10967
  • InChI=1/C2H4Cl2O/c3-1-5-2-4/h1-2H2
    Key: HRQGCQVOJVTVLU-UHFFFAOYAN
  • ClCOCCl
Properties
C2H4Cl2O
Molar mass 114.95 g·mol−1
Density 1.33 g/cm3
Melting point −41.5 °C (−42.7 °F; 231.7 K)
Boiling point 106 °C (223 °F; 379 K)
reacts[1]
Vapor pressure 30 mmHg (22°C)[1]
1.4421[2]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bis(chloromethyl) ether is an organic compound with the chemical formula (CH2Cl)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, but was found to be highly carcinogenic and thus such production has all but ceased.

Synthesis

It was produced industrially from paraformaldehyde and a mixture of chlorosulfonic acid and sulfuric acid.[3] It is also produced as a by-product in the Blanc chloromethylation reaction and is a known impurity in technical grade chloromethyl methyl ether.

Because of their carcinogenic potency, the industrial production of chloromethyl ethers ended in most countries in the early 1980s. Bis(chloromethyl) ether was no exception to this with production in the U.S.A. ending in 1982.

Uses

Bis(chloromethyl) ether has been extensively used in chemical synthesis, primarily as a crosslinking agent in the manufacture of ion-exchange resins and in the textile industry. It was also used as a linker in the synthesis of certain nerve agent antidotes (asoxime chloride, obidoxime). Bis(chloromethyl) was also effective for chloromethylation of aromatic substrates.[4]

Safety

Bis(chloromethyl) ether is carcinogenic.[5][6] It is one of 13 chemicals considered an OSHA-regulated occupational carcinogen.[7] Chronic exposure has been linked to in increased risk of lung cancer.[5]

See Also

References

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  1. ↑ 1.0 1.1 Cite error: Invalid <ref> tag; no text was provided for refs named PGCH
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Wilhelm Heitmann, Günther Strehlke, Dieter Mayer “Ethers, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a10_023
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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