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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; 1,1'-oxybis[2-chloroethane]
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
Flash point 55 °C; 131 °F; 328 K
Explosive limits 2.7%-?[1]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 15 ppm (90 mg/m3) [skin][1]
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N (what is checkY☒N ?)

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:[2]

Toxicity

Bis(chloroethyl) ether is extremely toxic, with a mechanism of action similar to mustard gas. It is a carcinogen.[3]

References

  1. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0196". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Pedersen, C. J. (1972). "Macrocyclic Polyethers: Dibenzo-18-Crown-6 Polyether and Dicyclohexyl-18-Crown-6 Polyether". Organic Syntheses. 52: 66; Collected Volumes, vol. 6, p. 395.
  3. ^ "Dichloroethyl ether". Documentation for Immediately Dangerous to Life or Health Concentrations (IDLH). CDC NIOSH. 1994. Retrieved 2012-10-17.
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