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Name Description
id 78
T3DB ID T3D0088
Name Bis(2-chloroethyl) ether
Class SmallMolecule
Description Bis(2-chloroethyl) ether (BCEE) is a colorless non-flammable liquid with a strong, unpleasant odor. It does not occur naturally, but is manufactured by humans for use in the production of pesticides and other chemicals. Limited amounts of BCEE dissolve in water and also slowly evaporate into air. In the environment, BCEE is broken down by bacteria in soil and water and by chemical reactions in the air, so it does not tend to persist for long periods. (L183)
Categories "Pesticide", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Industrial Precursor/Intermediate", "Organochloride", "Pesticide", "Ether", "Pollutant", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "1,1'-Oxybis(2-chloro)ethane", "1,1'-Oxybis(2-chloroethane)", "1,5-Dichloro-3-oxapentane", "1-Chloro-2-(.beta.-chloroethoxy)ethane", "1-Chloro-2-(2-chloroethoxy)ethane", "1-Chloro-2-(b-chloroethoxy)ethane", "1-Chloro-2-(beta-chloroethoxy)ethane", "2, 2'-Dichlorodiethyl ether", "2,2'-Dichlorethyl ether", "2,2'-Dichlorodiethyl ether", "2,2'-Dichlorodiethyl oxide", "2,2'-dichlorodiethylether", "2,2'-Dichloroethyl ether", "2-Chloroethyl ether", "b,b'-dichlorodiethyl ether", "b,b'-dichloroethyl ether", "b,b-dichlorodiethyl ether", "Beta ,beta'-dichlorodiethyl ether", "Beta,beta'-dichlorodiethyl ether", "Beta,beta-dichlorodiethyl ether", "Beta,beta-dichloroethyl ether", "Beta-chloroethyl ether", "Bis(.beta.-chloroethyl) ether", "Bis(2-chloroethyl)ether", "Bis(b-chloroethyl) ether", "Bis(beta-chloroethyl) ether", "Bis(chloro-2-ethyl) oxide", "Bis(chloroethyl) ether", "Bis(chloroethyl)ether", "Bis(chloroethyl)ether (bcee)", "Bis-2-chloroethylether", "Chlorex", "Chloroethyl ether", "Clorex", "Di(.beta.-chloroethyl) ether", "Di(2-chloroethyl) ether", "Di(b-chloroethyl) ether", "Di(beta-chloroethyl)ether", "Di(chloroethyl) oxide", "Dichlorodiethyl ether", "Dichloroether", "Dichloroethyl ether", "Dichloroethyl oxide", "Dicholoroethyl ether", "Diethylene glycol dichloride", "Oxybis(2-chloroethane)", "S-dichloroethyl ether", "SYM-dichloroethyl ether"
CAS Number 111-44-4
Chemical Formula C4H8Cl2O
Average Molecular Mass 143.01
Monoisotopic Mass 142.00
IUPAC Name 1-chloro-2-(2-chloroethoxy)ethane
Traditional Name BCEE
SMILES ClCCOCCCl
InChI Identifier InChI=1S/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2
InChI Key InChIKey=ZNSMNVMLTJELDZ-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Organooxygen Compounds
Class Ethers
Sub Class Dialkyl Ethers
Direct Parent Dialkyl Ethers
Alternate Parents "Organochlorides", "Alkyl Chlorides"
Geometric Description Aliphatic Acyclic Compounds
Substituents "organochloride", "alkyl chloride", "dialkyl ether", "Aliphatic Acyclic Compound", "Organohalogen Compound", "Alkyl Halide"
Descriptors
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cytoplasm", "Extracellular"
Biofluids
Tissues
Pathways
State Liquid
Appearance Colorless liquid.
Melting Point -51.9°C
Boiling Point
Solubility 17.2 mg/mL at 20 °C [VEITH,GD et al. (1980)]
LogP
Route of Exposure Oral (L184); inhalation (L184) ; dermal (L184)
Mechanism of Toxicity BCEE is extremely meabolized, with thiodiglycolic acid (TDGA) being the principal endproduct. The pathway leading to TDGA formation is uncertain, but probably involves oxidative cleavage of the ether bond to yield chloroacetaldehyde and 2-chloroethanol. (L183)
Metabolism BCEE is absorbed following inhalation exposure, oral administration, as well as contact to the skin. BCEE is distributed through the body, but highest levels are found in the liver, kidney and small intestine, while much lower levels are found in lung, spleen and muscle. BCEE is extensively metabolized to thiodiglycolic acid (TDGA), 2-chloroethoxyacetic acid (CEAA), and N-acetyl-S-[2-(2-chloroethoxy)ethyl]-L-cysteine, with TDGA being the principal endproduct. Smaller amounts of BCEE are metabolized by oxidation or substitution at a chlorine without ether cleavage. Approximately 80% of BCEE administered orally is excreted as TDGA within 48 hours. Smaller amounts are excreted in feces or expired air and only a very small fraction of the dose remains in the body. This indicates that BCEE is effectively excreted, and that it has a low tendency to accumulate in tissues. (L183, A129)
Toxicity
Lethal Dose
Carcinogenicity 3, not classifiable as to its carcinogenicity to humans. (L135)
Uses/Sources Bis(2-chloroethyl) ether is used in pesticides. It is also used as a solvent, cleaner, component of paint and varnish, rust inhibitor, or as a chemical intermediate to make other chemicals. Exposure occurs from consumption of drinking water that contains BCEE, breathing BCEE vapors, and dermal contact. (L183)
Minimum Risk Level Intermediate Inhalation: 0.02 ppm (L134)
Health Effects The principal acute effect of inhalation exposure to BCEE vapor is irritation and injury to the cells of the respiratory epithelium. BCEE vapors can cause loss of weight, nose irritation, severe injury to the lungs, and may lead to death. It might also cause cancer. (L183)
Symptoms Symptoms of BCEE exposure include coughing, sore throat, nausea, vomiting, burning sensation, redness of the exposed surface, laboured breathing, and abdominal pain, depending on the route of exposure. Symptoms may be delayed. (L184)
Treatment
DrugBank ID
HMDB ID
PubChem Compound ID 8115
ChEMBL ID CHEMBL1613350
ChemSpider ID 21106016
KEGG Compound ID C14688
UniProt ID 0
OMIM ID 0
ChEBI ID 0
BioCyc ID GAL-GLCNAC-GAL-GLC
CTD ID C006767
Stitch ID Bis(2-chloroethyl) ether
PDB ID
ACToR ID 169
Wikipedia Link
Creation Date 2009-03-06 18:58:03
Update Date 2014-12-24 20:21:05