Bis(chloroethyl) ether

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Bis(chloroethyl) ether
Bis(chloroethyl) ether.svg
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
Properties
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
Flash point 55 °C; 131 °F; 328 K
Explosive limits 2.7%-?[1]
Lethal dose or concentration (LD, LC):
77 ppm (rat, 4 hr)
152 ppm (mouse, 2 hr)
500 ppm (guinea pig, 1 hr)[2]
250 ppm (rat, 4 hr)
500 ppm (guinea pig, 5 hr)[2]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 15 ppm (90 mg/m3) [skin][1]
REL (Recommended)
Ca TWA 5 ppm (30 mg/m3) ST 10 ppm (60 mg/m3) [skin][1]
IDLH (Immediate danger)
Ca [100 ppm][1]
Related compounds
Related compounds
sulfur mustard
nitrogen mustard
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is YesYN ?)
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[edit]

Bis(chloroethyl) ether reacts with catechol to form dibenzo-18-crown-6:[3]

Synthesis of dibenzo-18-crown-6.png

Bis(chloroethyl) ether can be used in the synthesis of the cough suppressant fedrilate. It is combined with benzyl cyanide and two molar equivalents of sodamide in a ring-forming reaction.

Toxicity[edit]

Bis(chloroethyl) ether is extremely toxic, with a mechanism of action similar to sulfur mustard (being its oxygen analog). It is a carcinogen.[4]

See also[edit]

References[edit]

  1. ^ a b c d e f g h i j k "NIOSH Pocket Guide to Chemical Hazards #0196". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ a b "Dichloroethyl ether". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ 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 
  4. ^ "Dichloroethyl ether". Documentation for Immediately Dangerous to Life or Health Concentrations (IDLH). CDC NIOSH. 1994. Retrieved 2012-10-17.