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| 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 |
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| KEGG |
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| UNII | |
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| 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] |
Refractive index (nD) | 1.4421[2] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | carcinogen, reacts with water[1] |
| GHS labelling: | |
    | |
| Danger | |
| H225,H302,H311,H330,H350 | |
| Flash point | 38 °C (100 °F; 311 K) |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | OSHA-regulated carcinogen[1] |
REL (Recommended) | potential occupational carcinogen[1] |
IDLH (Immediate danger) | N.D.[1] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Bis(chloromethyl) ether is anorganic compound with the chemical formula (ClCH2)2O. It is a colourless liquid with an unpleasant suffocating odour and it is one of thechloroalkyl ethers. Bis(chloromethyl) ether was once produced on a large scale, but was found to be highlycarcinogenic and thus such production has ceased.
It was produced industrially fromparaformaldehyde and a mixture ofchlorosulfonic acid andsulfuric acid.[3] It is also produced as a byproduct in theBlanc chloromethylation reaction, formed when formaldehyde (the monomer, paraformaldehyde or formalin) and concentrated hydrochloric acid are mixed, and is a known impurity in technical gradechloromethyl 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.
Bis(chloromethyl) ether has been extensively used in chemical synthesis, primarily as a crosslinking agent in the manufacture ofion-exchange resins and in the textile industry. It was also used as a linker in the synthesis of certainnerve agent antidotes (asoxime chloride,obidoxime).Bis(chloromethyl) was also effective for chloromethylation of aromatic substrates.[4]
Bis(chloromethyl) ether iscarcinogenic.[5][6] It is one of 13 chemicals considered an OSHA-regulated occupational carcinogen.[7] Chronic exposure has been linked to in increased risk oflung cancer.[5]
It is classified as anextremely 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.[8]
