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List of IARC Group 3 Agents - Not classifiable as to its carcinogenicity to humans
Bis(chloroethyl) ether
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Bis(chloroethyl) ether

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Bis(chloroethyl) ether
Bis(chloroethyl) ether.svg
Names
Preferred 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
PubChem CID
RTECS number
  • KN0875000
UNII
UN number 1916
  • 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
Appearance Clear liquid
Odor Chlorinated, solvent-like
Density 1.22 g/mL
Melting point −50 °C; −58 °F; 223 K
Boiling point 178 °C; 352 °F; 451 K decomposes
10,200 mg/L
Vapor pressure 0.7 mmHg (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Very toxic (T+)
Dangerous for the environment (N)
Vesicant
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
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+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
4
1
1
Flash point 55 °C; 131 °F; 328 K
Explosive limits 2.7%-?
Lethal dose or concentration (LD, LC):
77 ppm (rat, 4 hr)
152 ppm (mouse, 2 hr)
500 ppm (guinea pig, 1 hr)
250 ppm (rat, 4 hr)
500 ppm (guinea pig, 5 hr)
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 15 ppm (90 mg/m3) [skin]
REL (Recommended)
 Ca TWA 5 ppm (30 mg/m3) ST 10 ppm (60 mg/m3) [skin]
IDLH (Immediate danger)
 Ca [100 ppm]
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 checkY☒N ?)

Bis(chloroethyl) ether is an organic compound with the formula O(CH2CH2Cl)2. It is an ether with two 2-chloroethyl substituents. It is a colorless liquid with the odor of a chlorinated solvent.

Reactions and applications

Bis(chloroethyl) ether is less reactive than the corresponding sulfur mustard S(CH2CH2Cl)2. In the presence of base, it reacts with catechol to form dibenzo-18-crown-6:

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. When treated with strong base, it gives divinyl ether, an anesthetic:

O(CH2CH2Cl)2 + 2 KOH → O(CH=CH2)2 + 2 KCl + 2 H2O

Toxicity

The LD50 is 74 mg/kg (oral, rat). Bis(chloroethyl) ether is considered as a potential carcinogen.

See also


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