trans-1,2-Dichloroethene (CHEM000157)

Record Information
Version1.0
Creation Date2009-03-06 18:58:13 UTC
Update Date2026-08-22 09:31:55 UTC
Accession NumberCHEM000157
Identification
Common Nametrans-1,2-Dichloroethene
ClassSmall Molecule
Description
Trans-1,2-dichloroethene (1,2-DCE) is one of two isomers of 1,2-dichloroethene. It is a highly flammable, colorless liquid with a sharp, harsh odor. 1,2-DCE is used as a solvent for waxes, resins, acetylcellulose, perfumes, dyes, lacquers, thermoplastics, fats, and phenols. It is also used as an intermediate in the preparation of other chlorinated solvents. (2, 3)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-1,2-DichloroethyleneChEBI
1,2-trans-DichloroethyleneChEBI
trans-1,2-DichloroethyleneChEBI
trans-Acetylene dichlorideChEBI
trans-DichloroethyleneChEBI
1,2-Dichloroethylene, (Z)-isomerMeSH
1,2-DichloroetheneMeSH
1,2-Dichloroethylene, (e)-isomerMeSH
1,2-DichloroethyleneMeSH
Chemical FormulaC2H2Cl2
Average Molecular Mass96.943 g/mol
Monoisotopic Mass95.953 g/mol
CAS Registry Number156-60-5
IUPAC Name(E)-1,2-dichloroethene
Traditional Nametrans-1,2-dichloroethylene
SMILESCl\C=C\Cl
InChI IdentifierInChI=1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1+
InChI KeyKFUSEUYYWQURPO-OWOJBTEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassVinyl halides
Sub ClassVinyl chlorides
Direct ParentVinyl chlorides
Alternative Parents
Substituents
  • Chloroalkene
  • Haloalkene
  • Vinyl chloride
  • Hydrocarbon derivative
  • Organochloride
  • 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-49.8°C
Boiling Point47.2 °C at 745 mm Hg 48.0 - 48.5 °C at 760 mm Hg
Solubility6.41 mg/mL at 25 °C [HORVATH,AL et al. (1999)]
Predicted Properties
PropertyValueSource
Water Solubility6.43 g/LALOGPS
logP1.85ALOGPS
logP1.74ChemAxon
logS-1.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.58 m³·mol⁻¹ChemAxon
Polarizability7.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureInhalation (2) ; oral (2) ; dermal (2) ; eye contact (2)
Mechanism of ToxicityTrans-1,2-dichloroethene is a volatile, lipophilic molecule that easily moves through the respiratory and gastrointestinal systems. It has a high affinity for lipids and blood, but little accumulation in tissues. 1,2-Dichloroethene isomers inhibit liver enzymes involved in metabolism and may increase the “toxic” response to other chemicals. Reactive metabolites of trans-1,2-dichloroethene modify the heme moiety of hepatic microsomal cytochrome P-450, resulting in a loss of both cytochrome P-450 and heme. Trans-1,2-dichloroethene can also mixed-function oxidase activities. Metabolism of trans-1,2-dichloroethene can lead to dose-related decrease in the levels of serum glutamicoxaloacetic transaminase (SGOT) and serum glutamic-pyruvic transaminase (SGPT). (2)
MetabolismMetabolism of trans-1,2-dichloroethene is initially catalyzed by hepatic microsomal cytochrome P-450. This metabolism is believed to involve epoxidation of the ethylene double bond, forming dichlorinated epoxides. Dichlorinated epoxides, in turn, can undergo a non-enzymatic rearrangement. Studies on the metabolism of 1,2-dichloroethene by hepatic microsomes and hepatocytes provide evidence to suggest that dichloroacetaldehyde is the predominant metabolite of microsomal cytochrome P-450 and that it, in turn, is extensively converted to dichloroethanol and dichloroacetate by cytosolic and/or mitochondrial aldehyde and alcohol dehydrogenases present in hepatocytes. (2)
Toxicity ValuesLD50: 1 300-10 000 mg/kg/day (Inhalation, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (1)
Uses/SourcesTrans-1,2-DCE is used as a solvent for waxes, resins, acetylcellulose, perfumes, dyes, lacquers, thermoplastics, fats, and phenols. It is also used as an intermediate in the preparation of other chlorinated solvents. One may be exposed by breathing contaminated air, eating, or drinking the substance, or by skin contact (2, 3).
Minimum Risk LevelAcute Inhalation: 0.2 ppm (Rat) (2) Acute Oral: 1 mg/kg/day (Rat) (2) Intermediate Oral: 0.3 mg/kg/day (2)
Health EffectsBreathing trans-1,2-DCE can cause sever liver and kidney damages, pulmonary capillary hyperemia, as well as alveolar septal distention; depression of the central nervous sustem can occur; moderate iritis and conjunctivitis can follow eye exposure; dermatitis and irritation of mucous membranes can follow dermal exposure. Symptoms associated with lethal oral doses included decreased activity, ataxia, suppressed or total loss of righting reflex, and depressed respiration. (2)
SymptomsSymptoms of trans-1,2-DCE exposure include nausea, dowiness, and tiredness. Mild or moderate erythema may follow dermal exposure, and skin or eye irritation can follow dermal/eye contact. (2)
TreatmentFollowing inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of seizures, administer a benzodiazepine IV. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes in case of eye exposure. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (4)
Concentrations
Not Available
External Links
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 LinkNot Available
Chemspider IDNot Available
ChEBI ID29027
PubChem Compound ID638186
Kegg Compound IDC06791
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References