Tetrachloroethylene (CHEM000029)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (38)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:57 UTC
Update Date2026-03-26 22:39:49 UTC
Accession NumberCHEM000029
Identification
Common NameTetrachloroethylene
ClassSmall Molecule
DescriptionTetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene ('perc'), and many other names, is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called 'dry-cleaning fluid.' It has a sweet odor detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about one million metric tons in 1985. Animal studies and a study of 99 twins by Dr. Samuel Goldman and researchers at the Parkinson's Institute in Sunnyvale, California determined there is a 'lot of circumstantial evidence' that exposure to tetrachloroethene increases the risk of developing Parkinson's disease ninefold. The International Agency for Research on Cancer has classified tetrachloroethene as a Group 2A carcinogen, which means that it is probably carcinogenic to humans. Like many chlorinated hydrocarbons, tetrachloroethene is a central nervous system depressant and can enter the body through respiratory or dermal exposure. Tetrachloroethene dissolves fats from the skin, potentially resulting in skin irritation. This reaction can be catalyzed by a mixture of potassium chloride and aluminium chloride or by activated carbon.
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2A
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cigarette Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1,2,2-TetrachloroethyleneChEBI
Ethylene tetrachlorideChEBI
PCEChEBI
PERCChEBI
PERKChEBI
TetrachloraethenChEBI
TetrachlorethyleneChEBI
TetrachloroethyleneChEBI
1,1,2, 2-TetrachloroethyleneHMDB
1,1,2,2-TetrachloroetheneHMDB
1,1,2,2-Tetrachloroethylene (acd/name 4.0)HMDB
AnkilostinHMDB
Antisal 1HMDB
Antisol 1HMDB
Carbon bichlorideHMDB
Carbon dichlorideHMDB
CzterochloroetylenHMDB
DidakeneHMDB
Dow-perHMDB
Fedal-unHMDB
NemaHMDB
Nema, veterinaryHMDB
PerawinHMDB
Perchloorethyleen, perHMDB
PerchlorHMDB
Perchloraethylen, perHMDB
PerchlorethyleneHMDB
Perchlorethylene, perHMDB
PerchloroetheneHMDB
PercleneHMDB
Perclene DHMDB
Perclene TGHMDB
PercloroetileneHMDB
PercosolveHMDB
PerkloneHMDB
PerSecHMDB
RCRA waste number u210HMDB
TetlenHMDB
TetracapHMDB
TetrachlooretheenHMDB
TetrachlorathenHMDB
Tetrachloro-etheneHMDB
Tetrachloro-ethyleneHMDB
TetrachloroetheneHMDB
TetracloroeteneHMDB
TetraguerHMDB
TetralenoHMDB
TetralexHMDB
TetravecHMDB
TetroguerHMDB
TetropilHMDB
PerchloroethyleneChEBI
Chemical FormulaC2Cl4
Average Molecular Mass165.833 g/mol
Monoisotopic Mass163.875 g/mol
CAS Registry Number127-18-4
IUPAC Nametetrachloroethene
Traditional Nameperchloroethylene
SMILESClC(Cl)=C(Cl)Cl
InChI IdentifierInChI=1S/C2Cl4/c3-1(4)2(5)6
InChI KeyCYTYCFOTNPOANT-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
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-22.3°C
Boiling PointNot Available
Solubility0.206 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP3.13ALOGPS
logP2.62ChemAxon
logS-2.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.78 m³·mol⁻¹ChemAxon
Polarizability11.6 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)splash10-02u0-4900000000-9854a27a57b089103a95Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02ce-9700000000-15e97c87ff2d3325dcdeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02u0-4900000000-9854a27a57b089103a95Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02ce-9700000000-15e97c87ff2d3325dcdeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0900000000-c9d94a196093a68ede77Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-8a7abc89fb2f94b90417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-8a7abc89fb2f94b90417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0900000000-8a7abc89fb2f94b90417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-8296157f9f0ba5c9a39fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-8296157f9f0ba5c9a39fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0900000000-8296157f9f0ba5c9a39fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-502fa884cfe21613d14cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-502fa884cfe21613d14cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-81606de257ffa3a01ba5Spectrum
MSMass Spectrum (Electron Ionization)splash10-02u0-2900000000-b8b0d0d4e84c9a237c39Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7) ; dermal (7)
Mechanism of ToxicityTetrachloroethylene is believed to affect the central nervous system by altering the fatty acid pattern of brain phospholipids and amino acids, or being incorporated into brain membranes, which may alter neural conduction velocity. Tetrachloroethylene's liver toxicity is caused mainly by its metabolite, trichloroacetic acid (TCA), which induces hepatocellular peroxisomes, causing DNA damage and leading to liver cancer. It is also thought to interfere specifically with energy-dependent hepatic transport functions by inhibiting cell membrane ATPases and decreasing hepatocyte ATP levels. (7, 1)
MetabolismTetrachloroethylene is readily absorbed following inhalation, oral, and dermal exposure. Once tetrachloroethylene is absorbed, its relatively high lipophilicity results in distribution to fatty tissue. Some tetrachloroethylene is metabolized to trichloroacetic acid (TCA) by cytochrome P-450 enzymes and the glutathione-conjugation pathway, then excreted in the urine. The remaining unmetabolized tetrachloroethylene is exhaled. (7)
Toxicity ValuesLD50: 3835 mg/kg (Oral, Rat) (7) LD50: 4678 mg/kg (Intraperitoneal, Rat) (11)
Lethal Dose2857 mg/kg for an adult human. (10)
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (9)
Uses/SourcesTetrachloroethylene is used for dry cleaning of fabrics and for metal-degreasing. It is also used to make other chemicals and is used in some consumer products, such as paint strippers and spot removers. (7)
Minimum Risk LevelAcute Inhalation: 2 ppm (8) Intermediate Inhalation: 0.1 ppm (8) Acute Oral: 0.2 mg/kg/day (8)
Health EffectsTetrachloroethylene is a central nervous system depressant. It is also known to cause liver and kidney damage, and is a probably carcinogen. (7)
SymptomsExposure to high concentrations of tetrachloroethylene can cause dizziness, headache, sleepiness, confusion, nausea, difficulty in speaking and walking, unconsciousness, and death. Irritation may result from repeated or extended skin contact with it. (7)
TreatmentTetrachloroethylene has no known antidote, and exposure is usually treated symptomatically. (7)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041980
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDTETRACHLOROETHENE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetrachloroethene
Chemspider ID13837281
ChEBI ID17300
PubChem Compound ID31373
Kegg Compound IDC06789
YMDB IDYMDB16084
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23416178
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23466729
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25042713
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25605280
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25690329
6. GRANDJEAN E, WANNER HU, RHINER A: [INVESTIGATIONS OF TETRACHLOROETHYLENE VAPORS IN 2 TYPES OF OPEN METAL CLEANING APPLIANCES]. Int Arch Gewerbepathol Gewerbehyg. 1964 Nov 3;21:69-79.
7. Braeckevelt M, Seeger EM, Paschke H, Kuschk P, Kaestner M: Adaptation of a constructed wetland to simultaneous treatment of monochlorobenzene and perchloroethene. Int J Phytoremediation. 2011 Nov-Dec;13(10):998-1013.
8. Tseng WJ, Guo SF: Synthesis of nanoporous Al2O3 membranes from polybutyl methacrylate functionalized SiO2 particles as a sacrificial template. J Nanosci Nanotechnol. 2012 Oct;12(10):7909-14.
9. Tsuruta H: Skin absorption of organic solvent vapors in nude mice in vivo. Ind Health. 1989;27(2):37-47.
10. Wroblewska K, Rogaczewska T: [Evaluation of occupational exposure to tetrachloroethylene (PER) in a dry cleaning business]. Med Pr. 1987;38(2):96-101.