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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 09:23:35 UTC
Update Date2019-07-23 05:46:18 UTC
HMDB IDHMDB0004811
Secondary Accession Numbers
  • HMDB04811
Metabolite Identification
Common Name2,4-Dichlorophenol
Description2,4-Dichlorophenol belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. It is produced on a large scale as a precursor to the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D).2,4-DCP is produced by chlorination of phenol. 2,4-Dichlorophenol (2,4-DCP) is a chlorinated derivative of phenol with the molecular formula Cl2C6H3OH. Liquid (molten) 2,4-DCP is readily absorbed through the skin. 2,4-Dichlorophenol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a white solid that is mildly acidic (pKa 7.9). 2,4-Dichlorophenol exists in all living species, ranging from bacteria to humans. 2,4-Dichlorophenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. This is primarily caused by instantaneous renal failure, liver damage and various other organ failure. It is also a photo-degradation product of the common antibacterial and antifungal agent triclosan along with the dioxin 2,8-dichlorodibenzo-p-dioxin. Annual worldwide production is estimated at 88 million pounds. The LD50 is 580 mg/kg (rats, oral).
Structure
Data?1563860778
Synonyms
ValueSource
24-DichlorophenolHMDB
1,3-Dichloro-4-hydroxybenzeneHMDB
2,4-Dichloro-phenolHMDB
2,4-DichlorophenateHMDB
2,4-Dichlorophenic acidHMDB
4,6-DichlorophenolHMDB
2,4-Dichlorophenol potassiumHMDB
2,4-Dichlorophenol, 14C-labeled CPDHMDB
2,4-Dichlorophenol sodiumHMDB
Chemical FormulaC6H4Cl2O
Average Molecular Weight163.001
Monoisotopic Molecular Weight161.963920164
IUPAC Name2,4-dichlorophenol
Traditional Name2,4-dichlorophenol
CAS Registry Number120-83-2
SMILES
OC1=CC=C(Cl)C=C1Cl
InChI Identifier
InChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
InChI KeyHFZWRUODUSTPEG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 4-chlorophenol
  • 2-chlorophenol
  • 2-halophenol
  • 4-halophenol
  • 1,3-dichlorobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aryl halide
  • Aryl chloride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.5 mg/mL at 20 °CNot Available
LogP3.06HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.49 g/LALOGPS
logP3.14ALOGPS
logP2.88ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.44ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.65 m³·mol⁻¹ChemAxon
Polarizability14.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9600000000-4fa477756aa23b7adcc6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9600000000-4fa477756aa23b7adcc6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2900000000-381e6453036090021608JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9740000000-cebcdb789d84c6207e03JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-f54ce3be94c6da8704e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9500000000-d8e24612e2f3f051febfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-95735b217c7349767bf6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-9600000000-4fa477756aa23b7adcc6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-94ffb74b937db7fcfcaaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-3ca52610ea3d01148575JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-50870879fea8dd32af55JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-0900000000-74b84ace3e15b790e691JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ed1f169a0b551f0c1b32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-ed1f169a0b551f0c1b32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-6781704e02cfe0c0c2ebJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03di-7900000000-cb2b5b10e5e1f6220386JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.00151(0.00128-0.00299) umol/mmol creatinineNot AvailableBothNormal
      • Report on Human B...
    details
    UrineDetected and Quantified0.00212(0.00124-0.00401) umol/mmol creatinineAdult (>18 years old)BothNormal
      • Report on Human B...
    details
    UrineDetected and Quantified0.0008 (0.0007-0.00088) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified0.000465 (0.000430-0.000506) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
      • 12031833
      • National Health a...
      • Report on Human B...
    details
    UrineDetected and Quantified0.000714 (0.000520-0.00101) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
      • 12031833
      • National Health a...
      • Report on Human B...
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB023422
    KNApSAcK IDNot Available
    Chemspider ID8140
    KEGG Compound IDC02625
    BioCyc ID24-DICHLOROPHENOL
    BiGG IDNot Available
    Wikipedia Link2,4-Dichlorophenol
    METLIN ID7075
    PubChem Compound8449
    PDB IDNot Available
    ChEBI ID16738
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceZiegler, Erich; Simmler, Inge. Acid condensation of 2,4-dichlorophenol with trioxymethylene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1941), 74B 1871-9.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Crespin MA, Gallego M, Valcarcel M: Solid-phase extraction method for the determination of free and conjugated phenol compounds in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jun 25;773(2):89-96. [PubMed:12031833 ]
    2. Ye X, Kuklenyik Z, Needham LL, Calafat AM: Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography-isotope dilution tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):110-5. Epub 2005 Dec 27. [PubMed:16377264 ]