Bis(chloroethyl) ether
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
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[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[1] decomposes
10,200 mg/L
Vapor pressure 0.7 mmHg (20 °C)[1]
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)
NFPA 704 four-colored diamond
4
1
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]
NIOSH (US health exposure limits):
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
2-Bromoethyl ether
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 ?)
Infobox references

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.[3]

Reactions and applications

Bis(chloroethyl) ether is less reactive than the corresponding sulfur mustard S(CH2CH2Cl)2.[3] In the presence of base, it reacts with catechol to form dibenzo-18-crown-6:[4]

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:[5]

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

Toxicity

The LD50 is 74 mg/kg (oral, rat).[3] Bis(chloroethyl) ether is considered as a potential carcinogen.[6]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 NIOSH Pocket Guide to Chemical Hazards. "#0196". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 "Dichloroethyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 3 Wang, Q. Q.; Begum, R. A.; Day, V. W.; Bowman-James, K. (2012). "Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity Wang, Qi-Qiang; Begum, Rowshan Ara; Day, Victor W.; Bowman-James, Kristin". Organic & Biomolecular Chemistry. 10 (44): 8786–8793. doi:10.1039/c2ob26482j. PMID 23070251. S2CID 9721325.
  4. ↑ Pedersen, C. J. (1972). "Macrocyclic Polyethers: Dibenzo-18-Crown-6 Polyether and Dicyclohexyl-18-Crown-6 Polyether". Organic Syntheses. 52: 66.; Collective Volume, vol. 6, p. 395
  5. ↑ Wollweber, Hartmund (2000). "Anesthetics, General". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_289. ISBN 978-3527306732.
  6. ↑ "CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): Dichloroethyl ether - NIOSH Publications and Products". www.cdc.gov. 2017-11-07. Retrieved 2018-10-31.
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