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Bis(chloromethyl) ether

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Bis(chloromethyl) ether
Bis(chloromethyl) ether.svg
Bis(chloromethyl)-ether-3D-balls.png
Names
Preferred IUPAC name
Chloro(chloromethoxy)methane
Other names
Bis(chloromethyl) ether
Bis-CME
Oxybis(chloromethane)
Bis-Chloromethyl ether
Chloromethyl ether
Dichlorodimethyl ether
Dichloromethyl ether
Identifiers
3D model (JSmol)
Abbreviations BCME
ChEBI
ChemSpider
ECHA InfoCard 100.008.030
EC Number
  • 208-832-8
KEGG
PubChem CID
UNII
  • 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
Vapor pressure 30 mmHg (22°C)
1.4421
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
carcinogen, reacts with water
GHS labelling:
H225, H302, H311, H330, H350
Flash point 38 °C (100 °F; 311 K)
NIOSH (US health exposure limits):
PEL (Permissible)
OSHA-regulated carcinogen
REL (Recommended)
potential occupational carcinogen
IDLH (Immediate danger)
N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 ceased.

Synthesis

It was produced industrially from paraformaldehyde and a mixture of chlorosulfonic acid and sulfuric acid. It is also produced as a byproduct in the Blanc chloromethylation reaction, formed when formaldehyde (the monomer, paraformaldehyde or formalin) and concentrated hydrochloric acid are mixed, 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.

Safety

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

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

See also


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