Bis(chloroethyl) ether

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
111-44-4 
ChemSpider 21106016 Yes
Jmol-3D images Image
Properties
Molecular formula
 C4H8Cl2O
Molar mass 143.01 g·mol−1
Appearance clear liquid[1]
Odor chlorinated, solvent-like[1]
Density 1.22 g/mL[1]
Melting point −50 °C; −58 °F; 223 K [1]
Boiling point 178 °C; 352 °F; 451 K decomposes
Negligible
Vapor pressure 0.7 mmHg (20°C)[1]
Hazards
Main hazards Very toxic (T+)
Dangerous for the environment (N)
Vesicant
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
1
4
1
Flash point 55 °C; 131 °F; 328 K
Explosive limits 2.7%-?[1]
US health exposure limits (NIOSH):
TWA 15 ppm (90 mg/m3) [skin][1]
Ca TWA 5 ppm (30 mg/m3) ST 10 ppm (60 mg/m3) [skin][1]
Ca [100 ppm][1]
Related compounds
Related compounds
 sulfur mustard
nitrogen mustard
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 
Infobox references

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]

See Also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 "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". Org. Synth. 52: 66.; Coll. Vol. 6, p. 395
  3. ↑ "Dichloroethyl ether". Documentation for Immediately Dangerous to Life or Health Concentrations (IDLH). CDC NIOSH. 1994. Retrieved 2012-10-17.