2-Chlorophenol (CHEM000214)

Record Information
Version1.0
Creation Date2009-03-06 18:58:21 UTC
Update Date2026-05-14 17:48:07 UTC
Accession NumberCHEM000214
Identification
Common Name2-Chlorophenol
ClassSmall Molecule
Description
2-Chlorophenol or ortho-chlorophenol is a monochlorophenol isomer that has a chlorine atom in the ortho position. It has a medicinal taste and smell, and is a slightly acidic liquid. 2-Chlorophenol is used as a disinfectant agent (3).
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • Sludge Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Disinfectant
  • Household Toxin
  • Organic Compound
  • Organochloride
  • Pollutant
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Chloro-1-hydroxybenzeneChEBI
O-ChlorophenolChEBI
O-MonochlorophenolHMDB
Ortho-chlorophenolHMDB
Ortho-monochlorophenolHMDB
2-MonochlorophenolHMDB
Chemical FormulaC6H5ClO
Average Molecular Mass128.556 g/mol
Monoisotopic Mass128.003 g/mol
CAS Registry Number95-57-8
IUPAC Name2-chlorophenol
Traditional Name2-chlorophenol
SMILESOC1=CC=CC=C1Cl
InChI IdentifierInChI=1S/C6H5ClO/c7-5-3-1-2-4-6(5)8/h1-4,8H
InChI KeyISPYQTSUDJAMAB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-chlorophenols. These are chlorophenols carrying a iodine at the C2 position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassHalophenols
Direct ParentO-chlorophenols
Alternative Parents
Substituents
  • 2-chlorophenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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 Descriptors
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
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point9.8°C
Boiling Point174.9°C
Solubility11.3 mg/mL at 25 °C [BANERJEE,S et al. (1980)]
Predicted Properties
PropertyValueSource
Water Solubility14.8 g/LALOGPS
logP2.4ALOGPS
logP2.27ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)7.97ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.84 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureInhalation (4) ; oral (4) ; dermal (4)
Mechanism of Toxicity2-chlorophenol works as a weak uncoupler of oxidative phosphorylation and inhibitors of cellular respiration. The ability of chlorophenols to uncouple oxidative phosphorylation increases with increasing chlorination. In fact, studies indicate a concentration-dependent triphasic effect of chlorophenols on phosphorylation and cellular respiration. At low concentrations, uncoupling produces stimulation of the resting state respiration as a result of increased adenosine triphosphatase (ATPase) activity in the absence of a phosphate acceptor.Inhibition of active respiration is also observed. At moderate concentrations, resting respiration is neither stimulated nor inhibited. Significant inhibition of respiration, associated with a breakdown of the electron transport process and decreased ATPase activity, occurs at very high concentrations. Uncoupling activity has been attributed to a protonophoric effect (a disruption of the energy gradient across the mitochondrial membrane resulting from distribution of chlorophenols in the phospholipid bilayer of the membrane), whereas inhibition of cellular respiration has been attributed to a direct action on intracellular proteins (2).
MetabolismAbsorption of 2-chlorophenol is favored in the stomach and the intestine. Absorption through the gastrointestinal tract is by simple diffusion and is expected to be both rapid and virtually complete.The metabolism of the 2-chlorophenol is principally via conjugation. The principal metabolite excreted is the glucuronide. Other metabolites are sulfate conjugates such as the ethereal sulfate. The metabobites are excreted in urine (2).
Toxicity ValuesLD50: 1000-1580 mg/kg (Dermal, Rabbit) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (1)
Uses/SourcesBreathing in contaminated air; drinking contaminated water; dermal and eye exposure (2).
Minimum Risk LevelNot Available
Health Effects2-chlorophenol is corrosive to epithelial tissue. It produce effects ranging from slight hyperemia to severe corrosion when applied to the corneas. Acute inhalation exposure may lead to hemorrhage in the lungs and tachypnea. Oral exposure to 2-chlorophenol can produce a variety of neurological effects, including tremors, myoclonic convulsions, a hunched posture, dyspnea, collapse, and coma (2).
SymptomsCough, shortness of breath and sore throat can result from inhalation of 2-chlorophenol. These symptoms may be delayed. Abdominal pain, drowsiness, weakness, and convulsions can result from ingestion as well as inhalation. Moreover, ingestion of 2-chlorophenol can cause restlessness, tremors, or central nervous system depression to occur. Eye exposure to 2-chlorophenol can lead to redness, pain, and blurred vision, while dermal contact can lead to redness and pain of the skin. Moreover, the substance can be rapidily absorbed after derma exposure (4).
TreatmentAvoid dilution following oral exposure; instead, administer charcoal as a slurry. Following inhalation, 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 the exposure occurs through eye contact, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. 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. (5)
Concentrations
Not Available
External Links
DrugBank IDDB03110
HMDB IDHMDB0245077
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link2-Chlorophenol
Chemspider ID13837686
ChEBI ID47083
PubChem Compound ID7245
Kegg Compound IDC14219
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.