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Record Information
Version1.0
Creation Date2009-03-06 18:58:03 UTC
Update Date2016-11-09 01:08:09 UTC
Accession NumberCHEM000079
Identification
Common Name1,2-Dichloroethane
ClassSmall Molecule
Description1,2-Dichloroethane is a solvent used in food processing.The chemical compound 1,2-dichloroethane, commonly known by its old name of ethylene dichloride (EDC), is a chlorinated hydrocarbon, mainly used to produce vinyl chloride monomer (VCM, chloroethene), the major precursor for PVC production. It is a colourless liquid with a chloroform-like odour. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. 1,2-Dichloroethane belongs to the family of Organochlorides. These are organic compounds containing a chlorine atom.
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
1,2-DCEChEBI
1,2-DichloraethanChEBI
alpha,beta-DichloroethaneChEBI
AethylenchloridChEBI
AethylendichloridChEBI
DCEChEBI
EDCChEBI
Ethane dichlorideChEBI
Ethylene chlorideChEBI
Ethylene dichlorideChEBI
Glycol dichlorideChEBI
a,b-DichloroethaneGenerator
Α,β-dichloroethaneGenerator
-DichloroethaneHMDB
alpha,BetHMDB
EDC, jmafHMDB
Ethylene dichloride, bsi, isoHMDB
R 150HMDB
S-DichloroethaneHMDB
Ethylene dichloride, 14C-labeledHMDB
Ethylene dichloride, 14c2-labeledHMDB
Ethylene dichloride, 38CL-labeledHMDB
Ethylene dichloride, ion (1+)HMDB
Ethylene dichloride, 36CL-labeledHMDB
Chemical FormulaC2H4Cl2
Average Molecular Mass98.959 g/mol
Monoisotopic Mass97.969 g/mol
CAS Registry Number107-06-2
IUPAC Name1,2-dichloroethane
Traditional Nameethylene dichloride
SMILESClCCCl
InChI IdentifierInChI=1S/C2H4Cl2/c3-1-2-4/h1-2H2
InChI KeyWSLDOOZREJYCGB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganochlorides
Sub ClassNot Available
Direct ParentOrganochlorides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organochloride
  • 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
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-35.3°C
Boiling Point83.5°C (182.3°F)
Solubility8.6 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility5.94 g/LALOGPS
logP1.48ALOGPS
logP1.5ChemAxon
logS-1.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.66 m³·mol⁻¹ChemAxon
Polarizability8.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-03dj-9000000000-88cef94bf1846b5d34d9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-03di-9000000000-9bbb890df5219b043356View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-03fr-9000000000-19f59c151d600b711587View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-03dj-9000000000-cbc052552f77ec2f97a6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-03di-9000000000-9bbb890df5219b043356View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-03fr-9000000000-19f59c151d600b711587View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-03dj-9000000000-cbc052552f77ec2f97a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-b5b7e1770ab8a271c6d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-fd57772305c022d82985View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-ddbe80583756fee90161View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-cb22ed7a81fc38732cd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-9000000000-f0ecd965b1dda1f68452View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9000000000-1fe65ee899de77eb1cbaView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-d96c34ebc6d42291a785View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureOral (7); inhalation (7) ; dermal (7)
Mechanism of Toxicity1,2-Dichloroethane is metabolized to 2-chloroacetaldehyde, S-(2-chloroethyl)glutathione by conjugation with glutathione, and to other putative reactive intermediates capable of binding covalently to cellular macromolecules in the liver, kidney, and other tissues. The conjugation of 1,2-dichloroethane with glutathione is catalyzed primarily by glutathione S-transferases. 1,2-Dichloroethane appears to be activated to mutagenic species to a lesser extent by the hepatic microsomal cytochrome P-450 enzyme system. Reactive metabolites of 1,2-dichloroethane produced by hepatic microsomal cytochrome P-450 can bind to cellular proteins and DNA. It has been suggested that 1,2-dichloroethane-induced toxicity occurs when the biotransformation processes are saturated, thereby allowing higher levels of 1,2-dichloroethane to circulate throughout the body and conjugate with glutathione instead of being detoxified and eliminated. (6, 1)
MetabolismDue to its physical properties such as its lipophilicity, 1,2-dichloroethane is likely to be absorbed across the alveolar membranes of the lung, mucosal membranes of the gastrointestinal tract, and the skin by passive diffusion. Once in the body, it is widely distributed, with the greatest amounts accumulating in the more lipophilic tissues. The primary route of biotransformation involves conjugation with glutathione to yield nonvolatile urinary metabolites. The other route, a cytocrome P-450-mediated oxidation is responsible for the formation of chloroacetaldehyde. Metabolic saturation appears to occur sooner after oral (gavage) administration than after inhalation exposure. Following inhalation or oral exposure, elimination of 1,2-dichloroethane occurs primarily via excretion of soluble metabolites in the urine and excretion of unchanged parent compound and carbon dioxide in the expired air. (6)
Toxicity ValuesLD50: 680 mg/kg (Oral, Rat) (6) LD50: 489-413 mg/kg (Oral, Mouse) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesThe most common use of 1,2-dichloroethane is in the production of vinyl chloride which is used to make a variety of plastic and vinyl products including polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. It is also used as a solvent and is added to leaded gasoline to remove lead. Exposure occurs mainly by breathing air or drinking water contaminated with 1,2-dichloroethane. Humans can be exposed to low levels of 1,2-dichloroethane through the skin or air by contact with old products made with 1,2-dichloroethane. (6)
Minimum Risk LevelChronic Inhalation: 0.6 ppm (4) Intermediate Oral: 0.2 mg/kg/day (4)
Health EffectsBreathing or swallowing large amounts of 1,2-dichloroethane can produce nervous system disorders, kidney diseases, or lung effects. This can also lead to heart failure. Skin lesions and benign pulmonary tumors were reported in animals exposed dermally to liquid 1,2-dichloroethane. 1,2-dichloroethane can cause death from cardiac arrhythmia, bronchitis, hemorrhagic gastritis and colitis, hepatocellular damage, renal tubular necrosis and calcification, central nervous system depression, and histological changes in brain tissue after a sufficient single oral dose. (6)
Symptoms1,2-Dichloroethane exposure causes abdominal pain, coughing, dizziness, drowsiness, headache, nausea, sore throat, diarrhea, unconsciousness, and vomiting, depending on the contact surface and the intensity. Redness of the eyes or skin occurs upon contact. (7)
TreatmentBlood gases should be monitored, a good ventilation maintained, and cardiac arrhythmias observed for a minimum of 24 hours. In the event of a ventricular arrhythmia, lidocaine or beta-blockers could be administered. Serum creatinine, hepatic aminotransferase, electrolytes, and fluid balance for signs of hepatic or renal failure should be monitored. Dialysis may be helpful in the event of renal failure. Hepatic failure may be treated with fresh frozen plasma, vitamin K, low protein diet, neomycin, and lactulose. (6)
Concentrations
Not Available
DrugBank IDDB03733
HMDB IDHMDB0029571
FooDB IDFDB000726
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID12-DICHLOROETHANE
METLIN IDNot Available
PDB IDDCE
Wikipedia Link1,2-Dichloroethane
Chemspider ID13837650
ChEBI ID27789
PubChem Compound ID11
Kegg Compound IDC06752
YMDB IDNot Available
ECMDB IDM2MDB004940
References
Synthesis Reference

Bruce E. Kurtz, Anatoli Omelian, “Apparatus for the production of ethylene dichloride.” U.S. Patent US3941568, issued October, 1970.

MSDSLink
General References
1. De Wildeman S, Neumann A, Diekert G, Verstraete W: Growth-substrate dependent dechlorination of 1,2-dichloroethane by a homoacetogenic bacterium. Biodegradation. 2003 Aug;14(4):241-7.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24228488
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24329990
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24441515