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Bis(chloroethyl) ether

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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
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.519 Edit this at Wikidata
EC Number
  • 203-870-1
KEGG
PubChem CID
RTECS number
  • KN0875000
UNII
UN number 1916
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2Key: ZNSMNVMLTJELDZ-UHFFFAOYSA-N
  • InChI=1/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2Key: ZNSMNVMLTJELDZ-UHFFFAOYAN
SMILES
  • ClCCOCCCl
Properties
Chemical formula C4H8Cl2O
Molar mass 143.01 g·mol
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
Solubility in water 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:
Pictograms GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H226, H300, H310, H315, H319, H330, H351
Precautionary statements 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 diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4 1 1
Flash point 55 °C; 131 °F; 328 K
Explosive limits 2.7%-?
Lethal dose or concentration (LD, LC):
LC50 (median concentration) 77 ppm (rat, 4 hr)
152 ppm (mouse, 2 hr)
500 ppm (guinea pig, 1 hr)
LCLo (lowest published) 250 ppm (rat, 4 hr)
500 ppm (guinea pig, 5 hr)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 15 ppm (90 mg/m)
REL (Recommended) Ca TWA 5 ppm (30 mg/m) ST 10 ppm (60 mg/m)
IDLH (Immediate danger) Ca
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 , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

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:

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

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0196". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Dichloroethyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  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; Collected Volumes, 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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