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Bis(chloroethyl) ether

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This is an old revision of this page, as edited by Cxtqrc (talk | contribs) at 19:34, 31 October 2018 (This is chemical is not "extremely toxic" and no evidence has shown it works as the way sulfur mustard does. Also, it is soluble in water thus its solubility is not "negligible".). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.
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 Edit this at Wikidata
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 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 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%-?[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
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 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 toxic when inhaled, and is considered as a potential carcinogen [4].

See also

References

  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 or 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; Collected Volumes, vol. 6, p. 395.
  4. ^ "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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