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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.519
EC Number 203-870-1
KEGG
RTECS number KN0875000
UNII
UN number 1916
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
GHS pictograms
GHS signal word Danger
H226, H300, H310, H315, H319, H330, H351
P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P281, P284, P301+310, P302+350, P302+352, P303+361+353, P304+340, P305+351+338, P308+313, P310, P320
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 4: Very short exposure could cause death or major residual injury. E.g., VX gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
4
1
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 ☑Y☒N ?)
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:[3]

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

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

References

  1. 1 2 3 4 5 6 7 8 9 "NIOSH Pocket Guide to Chemical Hazards #0196". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 "Dichloroethyl ether". Immediately Dangerous to Life and Health Concentrations (IDLH). 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". Organic Syntheses. 52: 66. ; Collective Volume, 6, p. 395
  4. ↑ "Dichloroethyl ether". Documentation for Immediately Dangerous to Life or Health Concentrations (IDLH). CDC NIOSH. 1994. Retrieved 2012-10-17.


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