Trichloroethylene (CHEM000014)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (50)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:55 UTC
Update Date2026-04-14 19:22:39 UTC
Accession NumberCHEM000014
Identification
Common NameTrichloroethylene
ClassSmall Molecule
DescriptionTrichloroethylene is a solvent and extractive in the manufacture of foods. One recent review of the epidemiology of kidney cancer rated cigarette smoking and obesity as more important risk factors for kidney cancer than exposure to solvents such as trichloroethylene. In contrast, the most recent overall assessment of human health risks associated with trichloroethylene states, [t]here is concordance between animal and human studies, which supports the conclusion that trichloroethylene is a potential kidney carcinogen. The evidence appears to be less certain at this time regarding the relationship between humans and liver cancer observed in mice, with the NAS suggesting that low-level exposure might not represent a significant liver cancer risk in the general population. The chemical compound trichloroethylene is a chlorinated hydrocarbon commonly used as an industrial solvent. It is a clear non-flammable liquid with a sweet smell. The first known report of TCE in groundwater was given in 1949 by two English public chemists who described two separate instances of well contamination by industrial releases of TCE. Based on available federal and state surveys, between 9% to 34% of the drinking water supply sources tested in the U.S. may have some TCE contamination, though EPA has reported that most water supplies are in compliance with the Maximum Contaminant Level (MCL) of 5 ppb. In addition, a growing concern in recent years at sites with TCE contamination in soil or groundwater has been vapor intrusion in buildings, which has resulted in indoor air exposures, such is in a recent case in the McCook Field Neighborhood of Dayton, Ohio. Trichloroethylene has been detected in 852 Superfund sites across the United States, according to the Agency for Toxic Substances and Disease Registry (ATSDR). Under the Safe Drinking Water Act of 1974, and as amended annual water quality testing is required for all public drinking water distributors. The EPA'S current guidelines for TCE can be found here. It should be noted that the EPA's table of TCE Releases to Ground is dated 1987 to 1993, thereby omitting one of the largest Superfund Cleanup sites in the nation, the NIBW in Scottsdale, Arizona. The TCE released here occurred prior to its appearance in the municipal drinking wells in 1982. This reaction can be catalyzed by a variety of substances. The most commonly used catalyst is a mixture of potassium chloride and aluminum chloride. However, various forms of porous carbon can also be used. This reaction produces tetrachloroethylene as a byproduct, and depending on the amount of chlorine fed to the reaction, tetrachloroethylene can even be the major product. Typically, trichloroethylene and tetrachloroethylene are collected together and then separated by distillation.Trichloroethylene: Parkinsonism and complex 1 mitochondrial neurotoxicity). Trichloroethylene is an effective solvent for a variety of organic materials. Trichloroethylene belongs to the family of Organochlorides. These are organic compounds containing a chlorine atom.
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • ECHA Carcinogen
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anesthetic
  • Cigarette Toxin
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,1-Dichloro-2-chloroethyleneChEBI
Acetylene trichlorideChEBI
Ethinyl trichlorideChEBI
Ethylene trichlorideChEBI
NarcogenChEBI
TCEChEBI
TrichlorChEBI
Trichloraethylenum pro narcosiChEBI
TrichloraethenChEBI
TrichloraethylenChEBI
TrichlorethyleneChEBI
TrichloroethylenumChEBI
TricieneChEBI
1,1,1-TrichloroethyleneHMDB
1,1,2-Trichloro-etheneHMDB
1,1,2-TrichloroetheneHMDB
1,1,2-TrichloroethyleneHMDB
1,2,2-TrichloroethyleneHMDB
1-Chloro-2,2-dichloroethyleneHMDB
AlgylenHMDB
Altene DGHMDB
AnamenthHMDB
BenzinolHMDB
BlacosolvHMDB
BlancosolvHMDB
C2HCL3HMDB
CecoleneHMDB
ChlorilenHMDB
ChloryleaHMDB
ChlorylenHMDB
ChorylenHMDB
CircosolvHMDB
CrawhaspolHMDB
Densi nfluatHMDB
DensinfluatHMDB
Disparit bHMDB
Distillex DS2HMDB
Dow-triHMDB
DukeronHMDB
Fleck-flipHMDB
Flock flipHMDB
FluateHMDB
GemalgeneHMDB
GermalgeneHMDB
LanadinHMDB
LethurinHMDB
NarkogenHMDB
NarkosoidHMDB
NialkHMDB
Perm-a-chlorHMDB
Perm-a-clorHMDB
PetzinolHMDB
PhilexHMDB
R 1120HMDB
Tce (chlorohydrocarbon)HMDB
ThrethylenHMDB
ThrethyleneHMDB
TrethyleneHMDB
TRIHMDB
Tri-cleneHMDB
Tri-plusHMDB
Tri-plus mHMDB
TrialHMDB
TriasolHMDB
Tric hloroetheneHMDB
TrichlooretheenHMDB
Trichloorethyleen, triHMDB
Trichloraethylen, triHMDB
TrichloraethylenumHMDB
TrichloranHMDB
TrichlorathaneHMDB
TrichlorenHMDB
TrichloretheneHMDB
Trichlorethylene, triHMDB
TrichlorethylenumHMDB
Trichloride, ethinylHMDB
Trichloro-etheneHMDB
Trichloro-ethyleneHMDB
TrichloroetheneHMDB
Trichloroethene, 9ciHMDB
Trichloroethylene (iupac)HMDB
Trichloroethylene (tce)HMDB
Trichloroethylene (with epichlorohydrin)HMDB
Trichloroethylene (without epichlorohydrin)HMDB
TrichlorotheneHMDB
TricloreteneHMDB
TricloroetileneHMDB
TricloroetilenoHMDB
TrieleneHMDB
TrielinHMDB
TrielinaHMDB
TrielineHMDB
Trik loneHMDB
TrikloneHMDB
Triklone NHMDB
TrilenHMDB
TrileneHMDB
Trilene te-141HMDB
TrilineHMDB
TrimarHMDB
TriolHMDB
VestrolHMDB
VitranHMDB
WestrosolHMDB
TrichloroethyleneChEBI
Chemical FormulaC2HCl3
Average Molecular Mass131.388 g/mol
Monoisotopic Mass129.914 g/mol
CAS Registry Number1979-01-06
IUPAC Name1,1,2-trichloroethene
Traditional Nametrichloroethylene
SMILESClC=C(Cl)Cl
InChI IdentifierInChI=1S/C2HCl3/c3-1-2(4)5/h1H
InChI KeyXSTXAVWGXDQKEL-UHFFFAOYSA-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
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-84.8°C
Boiling Point86.7°C (188.1°F)
Solubility1.28 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility1.96 g/LALOGPS
logP2.45ALOGPS
logP2.18ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.18 m³·mol⁻¹ChemAxon
Polarizability9.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9600000000-35bd416ad747042a0c53Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9800000000-152d0336467c74545ec4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03ea-9200000000-655b220bf877474e22b4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9600000000-35bd416ad747042a0c53Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001j-9800000000-152d0336467c74545ec4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03ea-9200000000-655b220bf877474e22b4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003v-7900000000-401c79c003cea991b031Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-1c5d55a90bcf42fd6a79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-54723e87d2cf07e437d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-2160348c43ed061e6433Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ddeffc3538dadd85ccfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-ddeffc3538dadd85ccfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-ddeffc3538dadd85ccfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-ebd2d5562c347d9a033cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-ebd2d5562c347d9a033cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-60c1e7d06db736d34d7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8c6a5ccbef32738aa756Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-c2fa753da65a4bac80a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4900000000-ba44c814cacfb3422385Spectrum
MSMass Spectrum (Electron Ionization)splash10-001j-9600000000-1c547ee123cf751604dcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (19) ; inhalation (19)
Mechanism of ToxicityThe toxic and carcinogenic effects of trichloroethylene are believed to be caused mainly by its metabolites, including trichloroacetic acid, dichloroacetic acid, and chloral hydrate. The nephrotoxicity and nephrocarcinogenicity of TRI have been attributed to glutathione conjunction, which forms reactive, sulfur-containing metabolites. Dichloroacetic acid is known to inhibit pyruvate dehydrogenase kinase, while chloral hydrate inhibits alcohol dehydrogenase. Studies in rodents have shown that neurotoxic effects may be caused by trichloroethylene's incorporation into brain membranes or ability to alter the fatty acid pattern of brain phospholipids and amino acids. One of the mechanisms of trichloroethylene's carcinogenicity is believed to be the peroxisome proliferation induced by its metabolites. (19, 24, 1)
MetabolismTrichloroethylene is absorbed into the bloodstream and rapidly distributed throughout the body. Some is metabolized via cytochrome P-450 enzymes and the glutathione-conjugation pathway into metabolites such as trichloroacetic acid and trichloroethanol, which are excreted primarily in the urine. However, most trichoroethylene is exhaled unchanged or as carbon dioxide. (20)
Toxicity ValuesLD50: 2402 mg/kg (Oral, Mouse) (25) LD50: 20 001 mg/kg (Dermal, Rabbit) (25) LD50: 3222 mg/kg (Intraperitoneal, Mouse) (25)
Lethal Dose3 to 5 mg/kg for an adult human. (23)
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (22)
Uses/SourcesTrichloroethylene is mainly used as an industrial solvent, particularily to remove grease from metal parts. It is also an ingredient in adhesives, paint removers, typewriter correction fluids, and spot removers. Exposure may result from contact with contaminated water. (19)
Minimum Risk LevelAcute Inhalation: 2 ppm (21) Intermediate Inhalation: 0.1 ppm (21) Acute Oral: 0.2 mg/kg/day (21)
Health EffectsChronic inhalation or ingestion of tricholoethylene causes nerve, kidney, and liver damage, impaired immune system function, impaired fetal development in pregnant women, and possibly death. It has also been linked to both kidney and liver cancer. (19)
SymptomsInhalation of trichloroethylene causes headaches, lung irritation, dizziness, poor coordination, and difficulty concentrating, while ingestion results in nausea. Larger amounts may cause unconciousness and impaired heart function. Skin contact often results in rashes. (19)
TreatmentThere is no known antidote for trichloroethylene. Exposure is usually handled with symptomatic treatment. (20)
Concentrations
Not Available
DrugBank IDDB13323
HMDB IDHMDB0029593
FooDB IDFDB000752
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrichloroethylene
Chemspider ID13837280
ChEBI ID16602
PubChem Compound ID6575
Kegg Compound IDC06790
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10459493
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11280697
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14780843
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15019957
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16641322
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24517489
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25278505
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=33930529
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=8319644
10. SCANSETTI G, RUBINO GF, TROMPEO G: [Study on chronic trieline poisoning. Note 3. Metabolism of trichloroethylene]. Med Lav. 1959 Dec;50:743-54.
11. Formica M, Vallero A, Forneris G, Cesano G, Pozzato M, Borca M, Iadarola GM, Quarello F: [Organohalogen contamination of a dialysis-water treatment plant]. G Ital Nefrol. 2002 Jul-Aug;19(4):479-82.
12. Cichocka D, Imfeld G, Richnow HH, Nijenhuis I: Variability in microbial carbon isotope fractionation of tetra- and trichloroethene upon reductive dechlorination. Chemosphere. 2008 Mar;71(4):639-48. Epub 2007 Dec 21.
13. Pistelli A, Masini E, Caramelli L, Botti P, Peruzzi S, Zorn AM, Mannaioni PF: [Acute toxicity of trichloroethylene. Description of a case series at the Autonomous Service of Toxicology of Florence during the 1977-1988 period]. Clin Ter. 1990 Nov 15;135(3):173-80.
14. BOKAY J, GOSZLETH T, GERGELY P: [Anesthesia with narcogen (trichloroethylene) in obstetrics]. Magy Noorv Lapja. 1955 Jan;18(1):30-43.
15. Ray K, Sahana CC, Chaudhuri SB, De GC, Chatterjee K: Effects of trichloroethylene anaesthesia on salivary paracetamol elimination. Indian J Physiol Pharmacol. 1993 Jan;37(1):79-81.
16. RUBINO GF, SCANSETTI G, TROMPEO G, GAIDO PC: [Study on chronic trieline poisoning. Note 4. Catabolism of derivatives of trichloroethylene]. Med Lav. 1959 Dec;50:755-65.
17. Guehl D, Bezard E, Dovero S, Boraud T, Bioulac B, Gross C: Trichloroethylene and parkinsonism: a human and experimental observation. Eur J Neurol. 1999 Sep;6(5):609-11.
18. Kostrzewski P, Jakubowski M, Kolacinski Z: Kinetics of trichloroethylene elimination from venous blood after acute inhalation poisoning. J Toxicol Clin Toxicol. 1993;31(2):353-63.
19. Eckerbom B, Lindholm CE: Performance evaluation of six heat and moisture exchangers according to the Draft International Standard (ISO/DIS 9360). Acta Anaesthesiol Scand. 1990 Jul;34(5):404-9.
20. Nystrom PO, Broome A, Hojer H, Ling L: A controlled trial of a plastic wound ring drape to prevent contamination and infection in colorectal surgery. Dis Colon Rectum. 1984 Jul;27(7):451-3.
21. VAN VLIET AG: [A case of toxic psychosis caused by trichloroethylene addiction]. Ned Tijdschr Geneeskd. 1959 Jan 10;103(2):75-8.
22. RUBINO GF, SCANSETTI G, TROMPEO G: [Study on chronic trieline poisoning. Note 2. Absorption of trichloroethylene]. Med Lav. 1959 Dec;50:733-42.
23. HEDGE HM: Occupational dermatitis of the nails and paronychia following use of permachlor diluted with methyl alcohol. Arch Derm Syphilol. 1948 Mar;57(3 Pt. 2):428.
24. HOLTORFF J: [Temporary report on our experiences in the use of the trichloroethylene compound chlorylene for inhalation analgesia in obstetrics]. Dtsch Gesundheitsw. 1952 Aug 14;7(33):1038-43.
25. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.