Bis(2-chloroethyl) ether (CHEM000082)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (38)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:03 UTC
Update Date2026-03-26 20:47:49 UTC
Accession NumberCHEM000082
Identification
Common NameBis(2-chloroethyl) ether
ClassSmall Molecule
DescriptionBis(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. (4)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,2'-Dichlorethyl etherKegg
1,5-Dichloro-3-oxapentaneKegg
ChlorexMeSH
Bis(2-chloroethyl)etherMeSH
Chemical FormulaC4H8Cl2O
Average Molecular Mass143.012 g/mol
Monoisotopic Mass141.995 g/mol
CAS Registry Number111-44-4
IUPAC Name1-chloro-2-(2-chloroethoxy)ethane
Traditional NameBCEE
SMILESClCCOCCCl
InChI IdentifierInChI=1S/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2
InChI KeyZNSMNVMLTJELDZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDialkyl ethers
Alternative Parents
Substituents
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-51.9°C
Boiling PointNot Available
Solubility17.2 mg/mL at 20 °C [VEITH,GD et al. (1980)]
Predicted Properties
PropertyValueSource
Water Solubility3.28 g/LALOGPS
logP1.23ALOGPS
logP1.45ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.7 m³·mol⁻¹ChemAxon
Polarizability13.65 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-95079a8a6fcae6bdb7deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-3900000000-f7c9de107866835737d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-673b6edfc1be1349c9fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-8db3ab7511714e5f327aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-5900000000-97682e358a8081af27f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9100000000-4cb3f81c096a2d8dde69Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-d87f696588501d4ebc6eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (5); inhalation (5) ; dermal (5)
Mechanism of ToxicityBCEE 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. (4)
MetabolismBCEE 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. (4, 1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (3)
Uses/SourcesBis(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. (4)
Minimum Risk LevelIntermediate Inhalation: 0.02 ppm (2)
Health EffectsThe 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. (4)
SymptomsSymptoms 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. (5)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBis(chloroethyl) ether
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID8115
Kegg Compound IDC14688
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available