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Bis(chloroethyl) ether

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Bis(chloroethyl) ether
Names
IUPAC name
1-Chloro-2-(2-chloroethoxy)ethane
Other names
Oxygen mustard; Bis(2-chloroethyl) ether; 2,2'-Dichlorodiethyl ether; Chlorex; Khloreks; DCEE; 2-Chloroethyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.519 Edit this at Wikidata
  • InChI=1S/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2 checkY
    Key: ZNSMNVMLTJELDZ-UHFFFAOYSA-N checkY
  • InChI=1/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2
    Key: ZNSMNVMLTJELDZ-UHFFFAOYAN
  • ClCCOCCCl
Properties
C4H8Cl2O
Molar mass 143.01 g·mol−1
Negligible
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Very toxic (T+)
Dangerous for the environment (N)
Vesicant
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
1
1
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

{{Chembox | ImageFile =2,2'-Dichlorodiethyl ether.svg | ImageSize = | ImageAlt = | IUPACName = | OtherNames = | Section1 = ! colspan=2 style="background: #f8eaba;color:inherit; text-align: center;" |Identifiers

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3D model (JSmol)

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| ECHA InfoCard | 100.003.519 Edit this at Wikidata |-




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  • C(CCl)OCCCl

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Bis(chloroethyl) ether is a chemical compound (an ether), which contains two 2-chloroethyl groups. It is a clear liquid with the odor of a chlorinated solvent.

Reactions

Bis(chloroethyl) ether reacts with catechol to form dibenzo-18-crown-6:[1]

Toxicity

Bis(chloroethyl) ether is extremely toxic, with a mechanism of action similar to mustard gas. It is a carcinogen.[2]

References

  1. ^ Charles J. Pedersen (1988). "Macrocyclic Polyethers: Dibenzo-18-Crown-6 Polyether and Dicyclohexyl-18-Crown-6 Polyether". Organic Syntheses; Collected Volumes, vol. 6, p. 395.
  2. ^ "CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): Dichloroethyl ether - NIOSH Publications and Products". Cdc.gov. Retrieved 2012-05-27.
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