ContaminantDB: 4-Chlorophenol

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

Record Information

Version

1.0

Creation Date

2009-06-15 17:16:04 UTC

Update Date

2026-03-31 19:07:39 UTC

Accession Number

CHEM000746

Identification

Common Name

4-Chlorophenol

Class

Small Molecule

Description

4-Chlorophenol or para-chlorophenol is a monochlorophenol isomer that has a chlorine atom in the para position. It is used as a disinfectant agent (2).

Contaminant Sources

My Exposome Chemicals
STOFF IDENT Compounds
Sludge Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Household Toxin
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
p-Chlorophenol	ChEBI
Parachlorophenol	ChEBI
4-Chlorophenol ion (1+)	MeSH
4-Chlorophenol, nickel (+2) salt	MeSH
4-Chlorophenol, titanium (+4) salt	MeSH
4-Chlorophenoxide	MeSH
Para-monochlorophenol	MeSH
4-Chlorophenol, copper (+1) salt	MeSH
4-Monochlorophenol	MeSH
4-Chlorophenol, potassium salt	MeSH
4-Chlorophenol, sodium salt	MeSH

Chemical Formula

C₆H₅ClO

Average Molecular Mass

128.556 g/mol

Monoisotopic Mass

128.003 g/mol

CAS Registry Number

106-48-9

IUPAC Name

4-chlorophenol

Traditional Name

chlorophenol

SMILES

OC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C6H5ClO/c7-5-1-3-6(8)4-2-5/h1-4,8H

InChI Key

WXNZTHHGJRFXKQ-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

4-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorophenol (CHEBI:28078 )
a chloroaromatic compound (CPD-10870 )

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.

Experimental Properties

Property	Value
Melting Point	42.8°C
Boiling Point	Not Available
Solubility	24 mg/mL at 25°C [ROBERTS,MS et al. (1977)]

Predicted Properties

Property	Value	Source
Water Solubility	14 g/L	ALOGPS
logP	2.37	ALOGPS
logP	2.27	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-6.3	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	32.84 m³·mol⁻¹	ChemAxon
Polarizability	12.02 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)	splash10-004i-8900000000-f5b8d40439248259fba6	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9800000000-3a8b74727039919cacc4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-7c45de518d13780605c4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-4855b919f4b9bab8519f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-9800000000-32ffdbba762c4f0fc609	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-4900000000-34735a026ba083fa0b7f	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 (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0900000000-edd6b8e255429561226b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0900000000-edd6b8e255429561226b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0900000000-4f6d51ee33067bb474ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0900000000-099706b387a703bff163	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-1900000000-51fe6ac2fa9bed9bb10a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-2900000000-a2fb225f178a8a1f4345	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9600000000-ec3022a622bccb6ec3fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-05r0-9400000000-1debf82a3dd9a5d2c117	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-05r3-9200000000-a2b07eb09c8d6ed52d74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0690-9100000000-657bec677b116442fc42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014l-9000000000-ad1f7056f8d05e405129	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gbc-9000000000-c791cec8d419b63d8d59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0690-9100000000-657bec677b116442fc42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-05r3-9200000000-a2b07eb09c8d6ed52d74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-05r0-9400000000-1debf82a3dd9a5d2c117	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0gbc-9000000000-c791cec8d419b63d8d59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014l-9000000000-ad1f7056f8d05e405129	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-0900000000-edd6b8e255429561226b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-004i-0900000000-4f6d51ee33067bb474ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-48f80a2ed99c319f28ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-a9a4905ea5907e304129	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9400000000-bf69c6609bd6a3690b0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-f67531a18d328dd39602	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-f67531a18d328dd39602	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9800000000-244eb0ef00d140eea0ab	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9600000000-55d86628a011109663e2	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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

Toxicity Profile

Route of Exposure

Inhalation (2) ; oral (2) ; dermal (2)

Mechanism of Toxicity

4-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).

Metabolism

Absorption of 4-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. It is proposed that 4-CP is metabolized by P-450 enzymes to intermediates that react with glutathione to form glutathionyl adducts.The metabolism of the 4-chlorophenol is principally via conjugation. The principal metabolite ecreted is the glucuronide. Other metabolites are sulfate conjugates such as the ethereal sulfate. The metabobites are excreted in urine (2).

Toxicity Values

LD50: 670 mg/kg (Oral, Rat) (3) LC50: 11 mg/m3 (Inhalation, Rat) (3)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (1)

Uses/Sources

Breathing in contaminated air; drinking contaminated water; dermal and eye exposure (2).

Minimum Risk Level

Acute Oral: 0.01 mg/kg/day (Rat) (2)

Health Effects

4-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).

Symptoms

Cough, 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 (2).

Treatment

Avoid 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. If 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. (4)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID