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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Sample Use Guides

In Vivo Use Guide
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
Record UNII
K18102WN1G
Record Status Validated (UNII)
Record Version