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
CAS Number	111-44-4 N
3D model (Jmol)	Interactive image
ChemSpider	21106016 Y
ECHA InfoCard	100.003.519
InChI InChI=1S/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2 Y Key: ZNSMNVMLTJELDZ-UHFFFAOYSA-N Y InChI=1/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2 Key: ZNSMNVMLTJELDZ-UHFFFAOYAN
SMILES ClCCOCCCl
Properties
Chemical formula	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
Solubility in water	Negligible
Vapor pressure	0.7 mmHg (20°C)
Hazards
Main hazards	Very toxic (T+) Dangerous for the environment (N) Vesicant
NFPA 704	1 4 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)
US health exposure limits (NIOSH):
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 YN ?)
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.

Bis(chloroethyl) ether 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.

Bis(chloroethyl) ether is extremely toxic, with a mechanism of action similar to mustard gas (being its oxygen isomer). It is a carcinogen.