Bis(chloromethyl) ether

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.

Bis(chloromethyl) ether
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
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[1]
Vapor pressure 30 mmHg (22°C)[1]
1.4421[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 carcinogen, reacts with water[1]
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[1]
REL (Recommended)
 potential occupational carcinogen[1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

It was produced industrially from paraformaldehyde and a mixture of chlorosulfonic acid and sulfuric acid.[3] 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.[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]

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.[8]

See also

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0128". National Institute for Occupational Safety and Health (NIOSH).
  2. Evans, L.; Gray, R. (May 1958). "Notes - Preparation of Certain Polychlorodimethyl Ethers". The Journal of Organic Chemistry. 23 (5): 745–746. doi:10.1021/jo01099a602.
  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. Olah, George A.; Beal, David A.; Olah, Judith A. (April 1976). "Aromatic substitution. XXXVIII. Chloromethylation of benzene and alkylbenzenes with bis(chloromethyl)ether, 1,4-bis(chloromethoxy)butane, 1-chloro-4-chloromethoxybutane, and formaldehyde derivatives". The Journal of Organic Chemistry. 41 (9): 1627–1631. doi:10.1021/jo00871a032.
  5. "Bis(chloromethyl)ether (BCME) (CASRN 542-88-1)". U.S. environmental protection agency. 2013-03-15. Retrieved 26 November 2014.
  6. Van Duuren, BL (August 1989). "Comparison of potency of human carcinogens: vinyl chloride, chloromethylmethyl ether and bis(chloromethyl)ether". Environmental Research. 49 (2): 143–51. Bibcode:1989ER.....49..143V. doi:10.1016/s0013-9351(89)80059-3. PMID 2526731.
  7. "NIOSH Pocket Guide to Chemical Hazards: bis-Chloromethyl ether". Centers for Disease Control and Prevention. Retrieved 26 November 2014.
  8. "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)
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