2,4-Dichlorophenol (T3D0209)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-03-06 18:58:17 UTC
Update Date2014-12-24 20:21:19 UTC
Accession NumberT3D0209
Identification
Common Name2,4-Dichlorophenol
ClassSmall Molecule
Description2,4-Dichlorophenol is a chlorinated organic chemical due to environmental exposure, that can be detected in breast milk. The free species of phenols and chlorinated organic appear to be most prevalent in milk (2).
Compound Type
  • Aromatic Hydrocarbon
  • Food Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1,3-Dichloro-4-hydroxybenzene
2,4-Dichloro-Phenol
2,4-Dichlorophenate
2,4-Dichlorophenic acid
4,6-Dichlorophenol
Chemical FormulaC6H4Cl2O
Average Molecular Mass163.001 g/mol
Monoisotopic Mass161.964 g/mol
CAS Registry Number120-83-2
IUPAC Name2,4-dichlorophenol
Traditional Name2,4-dichlorophenol
SMILESOC1=C(Cl)C=C(Cl)C=C1
InChI IdentifierInChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
InChI KeyInChIKey=HFZWRUODUSTPEG-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
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. (3)
Experimental Properties
PropertyValue
Melting Point45°C
Boiling Point210 °C
Solubility4.5 mg/mL at 20°C
LogP3.06
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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9600000000-4fa477756aa23b7adcc62017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9600000000-4fa477756aa23b7adcc62018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2900000000-381e64530360900216082016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9740000000-cebcdb789d84c6207e032017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-f54ce3be94c6da8704e52012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9500000000-d8e24612e2f3f051febf2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-95735b217c7349767bf62012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-03di-9600000000-4fa477756aa23b7adcc62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-94ffb74b937db7fcfcaa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-9300000000-ee63363c23d6239dcef62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0229-0900000000-4d6568956b7f0b03bf642021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-9200000000-06071826a250ba5266142021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-001i-9100000000-7d698141859118d007732021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-9500000000-e35d2e99fffd2ed1cb3b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-62d63d30b88cc774b3782021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-001i-9100000000-728df1b61fb336defed02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-001i-9100000000-a07532c1fc37fb84219b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-03di-0900000000-f970dd58417ca36c4e382021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0900000000-748a1d95a636ff7b4bf82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00di-2900000000-95fe1a59f9c6add130292021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-00dr-8900000000-c1b5887150f6182158872021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03ki-5900000000-fd43e6e802b61b3b34402021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001r-9000000000-5f091b1cd46578f4f17d2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-3ca52610ea3d011485752016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-50870879fea8dd32af552016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-0900000000-74b84ace3e15b790e6912016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-ed1f169a0b551f0c1b322016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-ed1f169a0b551f0c1b322016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-6781704e02cfe0c0c2eb2016-09-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-7900000000-cb2b5b10e5e1f62203862014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, benzene, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, benzene, experimental)Not Available2016-10-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-24View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureOral (3) ; dermal (3)
Mechanism of ToxicityChlorophenols have moderately high lipophilicity. Absorption through the gastrointestinal tract is by simple diffusion and is expected to be both rapid and virtually complete. The chlorophenols are also readily absorbed after dermal exposure. Chlorophenols uncouple mitochondrial oxidative phosphorylation and produce convulsions. At low concentrations, uncoupling produces stimulation of state 4 (resting state) respiration as a result of increased adenosine triphosphatase (ATPase) activity in the absence of a phosphate acceptor. Inhibition of state 3 (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. (3)
MetabolismAfter inhalation and dermal routes, 2,4-DCP is rapidly absorbed and excreted. Data on absorption following oral route are limited to animal studies. When administered intravenously to rats, 2,4-DCP rapidly distributes to the kidney, liver, fat, and brain, with the highest concentrations in the kidney and liver. 2,4-DCP strongly bind to serum proteins, including albumin and globulin. Both human and animal studies indicate that sulfation and glucuronidation are the main metabolic pathways of chlorophenols. 2,4-DCP has been shown to be metabolized into two major metabolites identified as 2-chloro-1,4-hydroxyquinone and 2-chloro-1,4-benzoquinone by microsomal fractions and whole cells of yeast Saccharomyces cerevisiae expressing human cytochrome P-450 3A4. Another metabolite, 1,2,4-hydroxybenzene, was also detected during biotransformation by whole cells but was not observed in microsomal fractions. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesChlorophenols are used as intermediates in the production of dyes and chlorinated pesticides. Exposed pesticide production workers may be at increased risk for soft tissue sarcoma, Hodgkin’s disease, and non-Hodgkin’s lymphoma. Most people are exposed to very low levels of chlorophenols from chlorinated drinking water. (3)
Minimum Risk LevelNot Available
Health EffectsDermally absorbed doses of chlorophenols are potentially more toxic than orally absorbed doses. Within 20 minutes of being accidentally splashed with 2,4-DCP on his right arm and leg, a worker experienced seizures, collapsed, and died shortly thereafter. Lethargy, tremors, convulsions, and/or central nervous system depression have been reported in chlorophenol-exposed animals. (3)
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB04811
PubChem Compound ID8449
ChEMBL IDCHEMBL1143
ChemSpider ID8140
KEGG IDC02625
UniProt IDNot Available
OMIM ID
ChEBI ID16738
BioCyc ID24-DICHLOROPHENOL
CTD IDC004762
Stitch ID2,4-Dichlorophenol
PDB IDNot Available
ACToR ID444
Wikipedia Link2,4-Dichlorophenol
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.
MSDSLink
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. [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. [16377264 ]
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for chlorophenols. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Androgen receptor
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Kim HJ, Park YI, Dong MS: Effects of 2,4-D and DCP on the DHT-induced androgenic action in human prostate cancer cells. Toxicol Sci. 2005 Nov;88(1):52-9. Epub 2005 Aug 17. [16107550 ]
  2. Li J, Ma M, Wang Z: In vitro profiling of endocrine disrupting effects of phenols. Toxicol In Vitro. 2010 Feb;24(1):201-7. doi: 10.1016/j.tiv.2009.09.008. Epub 2009 Sep 16. [19765641 ]
Target Details
2. Estrogen receptor beta
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Han DH, Denison MS, Tachibana H, Yamada K: Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. Biosci Biotechnol Biochem. 2002 Jul;66(7):1479-87. [12224631 ]
Target Details
3. Hepatocyte nuclear factor 4-alpha
General Function:
Zinc ion binding
Specific Function:
Transcriptionally controlled transcription factor. Binds to DNA sites required for the transcription of alpha 1-antitrypsin, apolipoprotein CIII, transthyretin genes and HNF1-alpha. May be essential for development of the liver, kidney and intestine.
Gene Name:
HNF4A
Uniprot ID:
P41235
Molecular Weight:
52784.205 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.59 uMATG_HNF4a_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]