ContaminantDB: 2,4-Dichlorophenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:17 UTC

Update Date

2026-08-23 09:56:00 UTC

Accession Number

CHEM000182

Identification

Common Name

2,4-Dichlorophenol

Class

Small Molecule

Description

2,4-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).

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2B
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
Sludge Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Metabolite
Organic Compound
Organochloride
PMT
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,4-Dichlorophenol potassium	MeSH
2,4-Dichlorophenol, 14C-labeled CPD	MeSH
2,4-Dichlorophenol sodium	MeSH
4,6-Dichlorophenol	MeSH
24-Dichlorophenol	ChEMBL, HMDB
1,3-dichloro-4-Hydroxybenzene	HMDB
2,4-dichloro-Phenol	HMDB
2,4-Dichlorophenate	HMDB
2,4-Dichlorophenic acid	HMDB

Chemical Formula

C₆H₄Cl₂O

Average Molecular Mass

163.001 g/mol

Monoisotopic Mass

161.964 g/mol

CAS Registry Number

120-83-2

IUPAC Name

2,4-dichlorophenol

Traditional Name

2,4-dichlorophenol

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 Key

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

dichlorophenol (CHEBI:16738 )
a chloroaromatic compound (24-DICHLOROPHENOL )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder. (4)

Experimental Properties

Property	Value
Melting Point	45°C
Boiling Point	210 °C
Solubility	4.5 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	2.49 g/L	ALOGPS
logP	3.14	ALOGPS
logP	2.88	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.44	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.65 m³·mol⁻¹	ChemAxon
Polarizability	14.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9600000000-4fa477756aa23b7adcc6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9600000000-4fa477756aa23b7adcc6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2900000000-381e6453036090021608	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9740000000-cebcdb789d84c6207e03	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-f54ce3be94c6da8704e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9500000000-d8e24612e2f3f051febf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-95735b217c7349767bf6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-03di-9600000000-4fa477756aa23b7adcc6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-03di-0900000000-94ffb74b937db7fcfcaa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-9300000000-ee63363c23d6239dcef6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0229-0900000000-4d6568956b7f0b03bf64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9200000000-06071826a250ba526614	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-001i-9100000000-7d698141859118d00773	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9500000000-e35d2e99fffd2ed1cb3b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-62d63d30b88cc774b378	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-001i-9100000000-728df1b61fb336defed0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-001i-9100000000-a07532c1fc37fb84219b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-03di-0900000000-f970dd58417ca36c4e38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03di-0900000000-748a1d95a636ff7b4bf8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00di-2900000000-95fe1a59f9c6add13029	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-00dr-8900000000-c1b5887150f618215887	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03ki-5900000000-fd43e6e802b61b3b3440	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001r-9000000000-5f091b1cd46578f4f17d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-3ca52610ea3d01148575	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-50870879fea8dd32af55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q9-0900000000-74b84ace3e15b790e691	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ed1f169a0b551f0c1b32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-ed1f169a0b551f0c1b32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-3900000000-6781704e02cfe0c0c2eb	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-7900000000-cb2b5b10e5e1f6220386	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; dermal (4)

Mechanism of Toxicity

Chlorophenols 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. (4)

Metabolism

After 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. (4)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

Chlorophenols 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. (4)

Minimum Risk Level

Not Available

Health Effects

Dermally 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. (4)

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0004811

FooDB ID

FDB023422

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

24-DICHLOROPHENOL

METLIN ID

7075

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Ziegler, Erich; Simmler, Inge. Acid condensation of 2,4-dichlorophenol with trioxymethylene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1941), 74B 1871-9.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10633543

2. Ziegler, Erich; Simmler, Inge. Acid condensation of 2,4-dichlorophenol with trioxymethylene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1941), 74B 1871-9.

3. Ziegler, Erich; Simmler, Inge. Acid condensation of 2,4-dichlorophenol with trioxymethylene. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1941), 74B 1871-9.

4. 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.

5. 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.

2,4-Dichlorophenol (CHEM000182)

Structure for CHEM000182: 2,4-Dichlorophenol