U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H5Cl
Molecular Weight 112.557
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Chlorobenzene

SMILES

ClC1=CC=CC=C1

InChI

InChIKey=MVPPADPHJFYWMZ-UHFFFAOYSA-N
InChI=1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H

HIDE SMILES / InChI

Molecular Formula C6H5Cl
Molecular Weight 112.557
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Chlorobenzene (MCB), C6H5Cl, is a colourless, volatile, water-insoluble, flammable liquid with a penetrating smell of almonds. Chlorobenzene belongs to the family of organic halogen compounds, which is a large class of natural and synthetic chemicals that contain one or more halogens (fluorine, chlorine, bromine, or iodine) combined with carbon and other elements. Chlorobenzene has been made from the chlorination of benzene since 1868. It has been manufactured industrially since the early 20 C. In the past, cholorobenzene was used to make phenol and DDT. Today, it is still used to produce pesticidesandchemicals used to prevent or kill unwanted pests. Chlorobenzene is also used as a high-boiling solvent in the manufacture of adhesives, paints, paint removers, polishes, dyes, and drugs. Human exposure to chlorobenzene appears to be primarily occupational. In urban areas, chlorobenzene may be released to the ambient air during its manufacture and use. Chronic exposure of humans to chlorobenzene affects the CNS. Signs of neurotoxicity include numbness,cyanosis, hyperesthesia (increased sensation), and muscle spasms. Headaches and irritation of the mucosa of the upper respiratory tract and eyes have also been reported in humans chronically exposed via inhalation. The CNS, liver, and kidneys have been affected in animals chronically exposed to chlorobenzene byinhalation. Chronic ingestion of chlorobenzene has resulted in damage to the kidneys and liver in animals. EPA has calculated a provisional Reference Concentration (RfC) of 0.02 milligrams per cubic meter (mg/m3) for chlorobenzene based on kidney and liver effects in rats. The Reference Dose (RfD) for chlorobenzene is 0.02 milligrams per kilogram body weight per day(mg/kg/d) based on histopathologic changes in the liver in dogs. EPA has medium confidence in the study on which the RfD was based because it provided both a no-observed-adverse-effect level (NOAEL) and a lowest-observed-adverse-effect level (LOAEL) andincorporated several biochemical and biological endpoints; medium confidence in the database becauseseveral subchronic, chronic, developmental, and reproductive toxicity studies provide supportive data, butthey did not give a complete assessment of toxicity; and, consequently, medium confidence in the RfD.

Approval Year

PubMed

PubMed

TitleDatePubMed
A novel biphasic extractive membrane bioreactor for minimization of membrane-attached biofilms.
2003-07-05
Stochastic simulation of hepatic preneoplastic foci development for four chlorobenzene congeners in a medium-term bioassay.
2003-06
Effects of FeS on the transformation kinetics of gamma-hexachlorcyclohexane.
2003-05-01
Time-gated pulsed glow discharge: real-time chemical speciation at the elemental, structural, and molecular level for gas chromatography time-of-flight mass spectrometry.
2003-05-01
A national survey of persistent, bioaccumulative, and toxic (PBT) pollutants in the United States milk supply.
2003-05
Selective ortho C-h activation of haloarenes by an Ir(I) system.
2003-04-23
Groundwater pollution and remediation options for multi-source contaminated aquifers (Bitterfeld/Wolfen, Germany).
2003-04-11
Cometabolic degradation of chlorinated aromatic compounds.
2003-04-10
3-Bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo.
2003-04-07
Evaluation of organics leaching from solidified/stabilized hazardous wastes using a powder reactivated carbon additive.
2003-04
[Advanced electrochemical oxidation process for treatment of biorefractory wastewater containing typical aromatic compounds].
2003-03
[Experimental study on the treatment of organic wastewater containing chlorobenzene by using an EGSB reactor].
2003-03
Development of a compact supersonic jet/multiphoton ionization/time-of-flight mass spectrometer for the on-site analysis of dioxin, part II: Application to chlorobenzene and dibenzofuran.
2003-03
Evolution of a chlorobenzene degradative pathway among bacteria in a contaminated groundwater mediated by a genomic island in Ralstonia.
2003-03
Hydrodehalogenation of chlorobenzene on activated carbon and activated carbon supported catalysts.
2003-03
Application of Fenton's reagent to regenerate activated carbon saturated with organochloro compounds.
2003-03
Kinetic study of the gas-phase hydrogenation of aromatic and aliphatic organochlorinated compounds using a Pd/Al2O3 catalyst.
2003-02-28
Photoluminescent metal-organic polymer constructed from trimetallic clusters and mixed carboxylates.
2003-02-24
Mechanistic and toxicokinetic data reducing uncertainty in risk assessment.
2003-02-18
Analytical procedure for the determination of chlorobenzenes in sediments.
2003-02
Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships.
2003-01-29
The effect of wet film thickness on VOC emissions from a finishing varnish.
2003-01-20
Membrane introduction mass spectrometry for monitoring complexation equilibria of beta-cyclodextrin with substituted benzenes.
2003-01
Dehalogenation potential of municipal waste incineration fly ash. II. Comparison of dehalogenation pathways of fly ash and model fly ash with thermodynamic calculations.
2003
Simultaneous sorption of lead and chlorobenzene by organobentonite.
2002-12
Antioxidant synergy and regeneration effect of quercetin, (-)-epicatechin, and (+)-catechin on alpha-tocopherol in homogeneous solutions of peroxidating methyl linoleate.
2002-11-20
Using different types of capillary chromatographic columns as denudation traps: a comparison of sorption properties.
2002-11-15
Demonstration of the "conditioning effect" in soil organic matter in support of a pore deformation mechanism for sorption hysteresis.
2002-11-01
Fiber introduction mass spectrometry: fully direct coupling of solid-phase microextraction with mass spectrometry.
2002-11-01
Solvent and concentration effects on the visible spectra of tri-para-dialkylamino-substituted triarylmethane dyes in liquid solutions.
2002-11
Evaluation of the parameters of 1:1 charge transfer complexes from spectrophotometric data by non-linear numerical method.
2002-11
Kinetics and mechanisms of ultrasonic degradation of volatile chlorinated aromatics in aqueous solutions.
2002-11
Sonolysis of chlorobenzene in Fenton-type aqueous systems.
2002-11
Gaseous contaminant emissions as affected by burning scrap tires in cement manufacturing.
2002-10-10
Compartment modeling of MTBE in the generic environment and estimations of the aquatic MTBE input in Germany using the EQC model.
2002-10
Charging and deforming the pybox ligand: enantiomerically pure double helices and their interconversion.
2002-09-16
Hydrogenolysis of chlorobenzene, dichlorobenzenes and chlorotoluenes by in situ generated and gaseous hydrogen in alkaline media and the presence of Pd/C catalyst.
2002-09
Dichloromethane alkylates a trithiolato-ruthenium complex to yield a methylene-bridged thioether core. Synthesis and structural comparison to the thiolato-ruthenium precursor.
2002-08-26
Volatile organic compounds cytotoxicity and expression of HSP72, HSP90 and GRP78 stress proteins in cultured human cells.
2002-08-19
Synthesis of adenosylcobinamide 2-chlorophenyl phosphate, a zwitterionic cobinamide phosphate analog of adenosylcobalamin en route to crystallizable cobinamides.
2002-08-15
Studies in sigmatropic rearrangement: synthesis of a [6,6]pyranothiopyran ring system by sequential claisen rearrangement and pyridine hydrotribromide mediated regioselective "6-Endo" cyclization.
2002-08-08
Microbial diversity in an in situ reactor system treating monochlorobenzene contaminated groundwater as revealed by 16S ribosomal DNA analysis.
2002-08
Temperature dependence of Henry's law constant in an extended temperature range.
2002-08
Analysis of photodecomposition of gaseous chlorobenzene by KrF excimer laser.
2002-08
Density-modified displacement for DNAPL source zone remediation: density conversion and recovery in heterogeneous aquifer cells.
2002-07-15
Numerical examination of the factors controlling DNAPL migration through a single fracture.
2002-07-13
Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. 1. Synthesis, structure-activity relationship, and biological effects of a new class of quinazoline derivatives.
2002-07-04
[Oxidative degradation of chlorinated hydrocarbons under anaerobic conditions].
2002-07
Kinetic and mechanistic investigation of the aminolysis of 3-methoxyphenyl 3-nitrophenyl thionocarbonate, 3-chlorophenyl 3-nitrophenyl thionocarbonate, and bis(3-nitrophenyl) thionocarbonate.
2002-06-14
Infrared detection of chlorinated hydrocarbons in water at ppb levels of concentrations.
2002-04
Patents

Sample Use Guides

Hepatotoxicity of bromobenzene (2 mmole/kg) in combination with toluene or chlorobenzene (4 mmole/kg each) were studied in vivo on the basis of GPT elevation and histological examinations. Both toluene and chlorobenzene suppressed bromobenzene hepatotoxicity 24 hr after the treatment, and chlorobenzene dramatically potentiated the toxicity at 48 hr. The glutathione level became lower at 12 hr and recovered at 24 hr when bromobenzene was given alone. The recovery delayed until 48 hr when chlorobenzene was coadministered.
Route of Administration: Unknown
In Vitro Use Guide
In experiments in vitro with microsomes from phenobarbital-pretreated rats, both toluene and chlorobenzene at 0.6 mM inhibited p-bromophenol formation noncompetitively but had no effect on o-isomer formation.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:28:17 GMT 2025
Edited
by admin
on Mon Mar 31 19:28:17 GMT 2025
Record UNII
K18102WN1G
Record Status Validated (UNII)
Record Version
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Name Type Language
Chlorobenzene
HSDB   MI  
Systematic Name English
NSC-8433
Preferred Name English
CHLOROBENZENE [HSDB]
Common Name English
MONOCHLORBENZENE
Common Name English
TETROSIN SP
Common Name English
CHLOROBENZENE [USP-RS]
Common Name English
PHENYL CHLORIDE
Systematic Name English
CHLOROBENZENE [MI]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 56504
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID4020298
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
RS_ITEM_NUM
1601361
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
WIKIPEDIA
CHLOROBENZENE
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
MESH
C031294
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
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NSC
8433
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
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FDA UNII
K18102WN1G
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
SMS_ID
100000172091
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-628-5
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
CAS
108-90-7
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
MERCK INDEX
m3392
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY Merck Index
PUBCHEM
7964
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
CHEBI
28097
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY
HSDB
55
Created by admin on Mon Mar 31 19:28:17 GMT 2025 , Edited by admin on Mon Mar 31 19:28:17 GMT 2025
PRIMARY