2,3,4,5-Tetrachlorophenol (CHEM000160)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:13 UTC
Update Date2026-03-31 18:15:04 UTC
Accession NumberCHEM000160
Identification
Common Name2,3,4,5-Tetrachlorophenol
ClassSmall Molecule
Description2,3,4,5-Tetrachlorophenol is one of several chlorophenol isomers. It is a solid with a strong medicinal taste and odor, and small amounts can be tasted in water. (3)
Contaminant Sources
  • My Exposome Chemicals
  • Sludge Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy-2,3,4,5-tetrachlorobenzeneChEBI
2,3,4,5-TeCPChEBI
2,3,4,5-TetrachlorophenateHMDB
Chemical FormulaC6H2Cl4O
Average Molecular Mass231.891 g/mol
Monoisotopic Mass229.886 g/mol
CAS Registry Number25167-83-3
IUPAC Name2,3,4,5-tetrachlorophenol
Traditional Name2,3,4,5-tetrachlorophenol
SMILESOC1=CC(Cl)=C(Cl)C(Cl)=C1Cl
InChI IdentifierInChI=1S/C6H2Cl4O/c7-2-1-3(11)5(9)6(10)4(2)8/h1,11H
InChI KeyRULKYXXCCZZKDZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-chlorophenols. These are chlorophenols carrying a iodine at the C4 position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassHalophenols
Direct ParentP-chlorophenols
Alternative Parents
Substituents
  • 4-chlorophenol
  • 2-chlorophenol
  • 3-chlorophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Halobenzene
  • Chlorobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.092 g/LALOGPS
logP4.41ALOGPS
logP4.09ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.33ChemAxon
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.26 m³·mol⁻¹ChemAxon
Polarizability18.37 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-1090000000-8c331f56bd7350213e14Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-2b2e90a272193595d84aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090000000-2b2e90a272193595d84aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0090000000-7e4ef7faea42fdf947f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-a60abdd1a3c21cd713ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-bae18e70ded54ce1cb73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-1b4b0f92db076642d338Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-1a6c06d5976fc728165dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090000000-1a6c06d5976fc728165dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0190000000-0275c8881ee52e53cd5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-dba09e38f682b17a1153Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-95eea68de2fe05ac6483Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00pi-8590000000-052631685194549d87fcSpectrum
Toxicity Profile
Route of ExposureInhalation (3) ; oral (3) ; dermal (3) ; eye contact (3)
Mechanism of ToxicityTetrachlorophenols decrease or block ATP production without blocking the electron transport chain. Thus the poisons uncouple phosphorylation from oxidation. Free energy from the electron transport chain then converts to more body heat. As body temp rises, heat-dissipating mechanisms are overcome and metabolism is speeded. More ADP and other substrates accumulate, and these substrates stimulate the electron transport chain further. The electron transport chain responds by using up more and more available oxygen (increasing oxygen demand) in an effort to produce ATP, but much of the free energy generated is liberated as still more body heat. Oxygen demand quickly overcomes oxygen supply, and energy reserves become depleted. (1)
MetabolismTetrachlorophenols are rapidly absorbed and excreted following occupational exposure, which involves both the inhalation and dermal routes. Most of the 2,3,4,5-tetrachlorophenol is excreted unchanged in the urine; trichlorohydroquinone has been identified as one of its metabolites. (3)
Toxicity ValuesLD50: >2000 mg/kg (Dermal, Rabbit) (3) LD50: 400 mg/kg/day (Oral, Mouse) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not directly listed by IARC, but related polychlorophenols are discussed, and combined exposures to polychlorophenols or to their sodium salts are classified as possibly carcinogenic to humans (Group 2B). (2)
Uses/SourcesExposure may result from breathing contaminated air, ingesting contaminated water or foods, and skin or eye contact, particularly while treating wood. (3)
Minimum Risk LevelAcute Oral: 0.01 mg/kg/day (Rat) (3) Intermediate Oral: 0.003 mg/kg/day (Rat) (3)
Health EffectsDermal exposure can cause corrosive skin damage. (3)
SymptomsDust has been found irritating to the nose and throat. Skin or eye contact can cause irritation of the exposed surface. Clinical signs preceding death for all tetrachlorophenol isomers included initial hyperactivity followed by hypoactivity, neuromuscular weakness, and convulsions. Headache can also result from exposure to 2,3,4,5-tetrachlorophenol. (3)
TreatmentIn case of oral exposure, dilution may enhance absorption of phenol and should be avoided, but charcoal may be administered. If methemoglobinemia occurs, administer 1 to 2 mg/kg of 1% methylene blue slowly IV in symptomatic patients. Additional doses may be required. If hypotension occurs, infuse 10 to 20 mL/kg isotonic fluid. If hypotension persists, administer dopamine or norepinephrine. Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress, and 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. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes following eye exposure. Following dermal exposure, remove phenol with undiluted polyethylene glycol 300 to 400 or isopropyl alcohol prior to washing, if readily available. Wash exposed areas twice or for at least 10 minutes with large quantities of soapy water. Water alone may be harmful. (4)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0245429
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 ID19766
ChEBI ID132357
PubChem Compound ID21013
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1260504
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18970864
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2219952
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23123243
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4046067
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=50558
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=580377
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6991923
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7445521
10. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.