4-Chlorophenol

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H5ClO
Molecular Weight	128.556
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(Cl)C=C1

InChI

InChIKey=WXNZTHHGJRFXKQ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H5ClO
Molecular Weight	128.556
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.researchgate.net/publication/253349096_p-Chlorophenoxyacetic_acid_-_Preparation_of_a_synthetic_plant_hormone | http://www.guidechem.com/reference/dic-371673.htmlhttp://www.ncbi.nlm.nih.gov/pubmed/5270931
Curator's Comment: Description was created based on several sources, including http://drugs-about.com/drugs-e/endotine.html and http://www.ncbi.nlm.nih.gov/pubmed/1337555

Parachlorophenol is a disinfectant effective against most gram-negative organisms, it is currently used in endodontic therapy in a 35 per cent concentration as camphorated parachlorophenol for the disinfection of root canals. It is marketed under the brand name Endotine in France.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
macrophage activation involved in immune response 3 Target ID: GO:0002281 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9487846	Inhibitor 8504
Enterococcus faecalis growth 2 Target ID: Enterococcus faecalis growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/9590928	Inhibitor 8504
Porphyromonus gingivalis growth 2 Target ID: Porphyromonus gingivalis growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/1337555	Inhibitor 8504
Fusobacterium nucleatum growth 2 Target ID: Fusobacterium nucleatum growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/1337555	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dental pulp disorder 2 Sources: http://www.guidechem.com/reference/dic-371673.html	Primary		Not Provided 511	Unknown Approved Use Unknown
Bacterial Infections of root canal 2 Sources: http://www.doctissimo.fr/medicament-ENDOTINE.htm	Curative		Approved 8583	Endotine Approved Use Root canal antiseptic

PubMed

Title	Date	PubMed
Urinary excretion of chlorinated phenols in saw-mill workers.	1991	1856025
Degradation of 2,3,4,6-tetrachlorophenol at low temperature and low dioxygen concentrations by phylogenetically different groundwater and bioreactor bacteria.	2001	11995822
Strategies to enhance the biodegradation of toxic compounds using discontinuous processes.	2001	11381918
Photochemical oxidation of p-chlorophenol by UV/H2O2 and photo-Fenton process. A comparative study.	2001	11150131
Toxicity of mono-, di- and tri-chlorophenols to lux marked terrestrial bacteria, Burkholderia species Rasc c2 and Pseudomonas fluorescens.	2001 Apr	11297395
An isomer prediction model for PCNs, PCDD/Fs, and PCBs from municipal waste incinerators.	2001 Aug 1	11505998
Internal exposure to polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans (PCDDs/PCDFs) of Bavarian chimney sweeps.	2001 Jan	11116349
Sonochemical degradation for toxic halogenated organic compounds.	2001 Jul	11441605
In vivo gene delivery into ocular tissues by eye drops of poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) (PEO-PPO-PEO) polymeric micelles.	2001 Jul	11438834
In situ polychlorophenol bioremediation potential of the indigenous bacterial community of boreal groundwater.	2001 Jul	11394785
Purification and catalytic properties of the chlorophenol 4-monooxygenase from Burkholderia cepacia strain AC1100.	2001 Jun 11	11410285
[Adsorption of p-chlorophenol by biofilm and its components].	2001 Mar	11432061
Electrochemical oxidation of para-chlorophenol on Ti/SnO2-PbO2 electrodes: introduction of a parameter for the estimation of their efficiency.	2001 Mar-Apr	11381540
Rapid determination of nineteen chlorophenols in wood, paper, cardboard, fruits, and fruit juices by gas chromatography/mass spectrometry.	2001 May-Jun	11417649
Development of an element-selective monitoring system for adsorbable organic halogens (AOX) with plasma emission spectrometric detection for quasi-continuous waste-water analysis.	2001 Nov	11767887
A GAC biofilm reactor for the continuous degradation of 4-chlorophenol: treatment efficiency and microbial analysis.	2001 Oct	11759696
Suitability of the trans/cis ratio of unsaturated fatty acids in Pseudomonas putida NCTC 10936 as an indicator of the acute toxicity of chemicals.	2001 Sep	11534954
Adsorption of phenol and m-chlorophenol on organobentonites and repeated thermal regeneration.	2002	12214970
[Prophylactic efficiency of tietasol and oxymethyluracyl against chlorphenols exposure in experimental and real conditions].	2002	12087819
Variation of toxicity during the ozonation of monochlorophenolic solutions.	2002	11846283
Detection of insulin-regulated GLUT4-translocation by the insertion of a protein C epitope in L6 myoblasts.	2002 Apr 18	12062111
Lethal body residue of chlorophenols and mixtures of chlorophenols in benthic organisms.	2002 Aug	12115047
Effects of parachlorophenol and camphorated parachlorophenol on the phagocytic activities of a murine macrophage cell line (RAW264.7).	2002 Dec	12489648
Dechlorination of chlorinated phenols by catalyzed and uncatalyzed Fe(0) and Mg(0) particles.	2002 Feb 14	11777595
Effects of 2,4-dichlorophenol on activated sludge.	2002 Jul	12111171
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.	2002 Jul 15	12076687
Acute toxicity of crude and dispersed oil to Octopus pallidus (Hoyle, 1885) hatchlings.	2002 Jun	12146864
Adsorption of phenolic compounds from aqueous solutions by a water-compatible hypercrosslinked polymeric adsorbent.	2002 Jun	12108706
Kinetic modeling of fenton oxidation of phenol and monochlorophenols.	2002 Jun	12108698
Acute lethal toxicity of environmental pollutants to aquatic organisms.	2002 Jun	12061826
Porous polysilsesquioxanes for the adsorption of phenols.	2002 Jun 1	12075813
Impact of protein binding on the availability and cytotoxic potency of organochlorine pesticides and chlorophenols in vitro.	2002 Jun 14	12049848
Spatial distibution and temporal accumulation of polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls in the Gulf of Finland.	2002 Jun 15	12099450
[Degradation of 4-chlorophenol in aqueous solution by high-voltage pulsed discharge-ozone technology].	2002 Mar	12048824
Dimethyl sulfoxide blocks herpes simplex virus-1 productive infection in vitro acting at different stages with positive cooperativity. Application of micro-array analysis.	2002 May 24	12052246
Solar photocatalysis: a clean process for water detoxification.	2002 May 27	12150445
Identification of 2,4-dichlorophenol in females of the American dog tick, Dermacentor variabilis (Acari: Ixodidae), and its possible role as a component of the attractant sex pheromone.	2002 Nov	12495199
Separation and determination of phenolic compounds by capillary electrophoresis with chemiluminescence detection.	2002 Nov 29	12458957
Thermodynamic study of adsorption of phenolic compounds onto Amberlite XAD-4 polymeric adsorbents and its acetylized derivative MX-4.	2002 Oct	12491718
Development of supercritical fluid extraction with a solid-phase trapping for fast estimation of toxic load of polychlorinated dibenzo-p-dioxins-dibenzofurans in sawmill soil.	2002 Oct 25	12458759
The role of hydrogen bonding on the h-atom-donating abilities of catechols and naphthalene diols and on a previously overlooked aspect of their infrared spectra.	2002 Oct 30	12392436
Concentration of chlorophenols in water with sodium dodecylsulfate-gamma-alumina admicelles for high-performance liquid chromatographic analysis.	2002 Oct 4	12416878
Detoxification of phenolic solutions with horseradish peroxidase and hydrogen peroxide.	2002 Sep	12405413
Expression of beta-galactosidase by recombinant respiratory syncytial viruses for microneutralization assay.	2002 Sep	12270661
Degradation of 4-chlorophenol by the white rot fungus Phanerochaete chrysosporium in free and immobilized cultures.	2002 Sep	12139330
Retroviral vectors for establishing tetracycline-regulated gene expression in an otherwise recalcitrant cell line.	2002 Sep 3	12392602
Simulation of bioremediation of chlorophenols in a sandy aquifer.	2003 Jan	12465806
Hard coal as a potential low-cost adsorbent for removal of 4-chlorophenol from water.	2016	27120657

Patents

Sample Use Guides

In Vivo Use Guide

Male mice were administered 4-Chlorophenol, 1.5 mmol/kg body weight, i.p.

Route of Administration: Intraperitoneal

In Vitro Use Guide

In fibroblast L929 cells the effective concentration for half-maximal response (EC50 value at 24 h for 4-Chlorophenol is 2.18 mmol/L and the EC50 value at 48 h is 1.18 mmol/L by using 3-(4,5-dimethylthiazd-2-yl)-2,5-diphenyltentrazolium bromide (MTT) reduction assay.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:04 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:04 GMT 2025`
Record UNII	3DLC36A01X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

p-Chlorophenol

Preferred Name

English

4-Chlorophenol

Systematic Name

English

PARACHLOROPHENOL [USP-RS]

Common Name

English

PARACHLOROPHENOL [VANDF]

Common Name

English

4-Chlorphenol [WHO-DD]

Common Name

English

PARACHLOROPHENOL [MART.]

Common Name

English

Parachlorophenol

Systematic Name

English

PARACHLOROPHENOL [USP MONOGRAPH]

Common Name

English

PARACHLOROPHENOL [HSDB]

Common Name

English

P-CHLOROPHENOL [MI]

Common Name

English

PARACHLOROPHENOL [JAN]

Common Name

English

NSC-2877

Code

English

4-CHLORPHENOL

Common Name

English

PHENOL, 4-CHLORO-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28394