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Name Description
id 91
T3DB ID T3D0104
Name Chlorobenzene
Class SmallMolecule
Description Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals. Rhodococcus phenolicus is a bacterium species able to degrade chlorobenzene as sole carbon sources. Chlorobenzene exhibits low to moderate toxicity as indicated by its LD50 of 2.9 g/kg. Chronic (long-term) exposure of humans to chlorobenzene affects the central nervous system (CNS). Signs of neurotoxicity in humans include numbness, cyanosis, hyperesthesia (increased sensation), and muscle spasms.
Categories "Pesticide", "Household Toxin", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Industrial Precursor/Intermediate", "Organochloride", "Aromatic Hydrocarbon", "Solvent", "Pesticide", "Pollutant", "Metabolite", "Household Toxin", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "6-Chlorobenzene-1,2,4-triol", "6-Chlorohydroxyquinol", "Abluton T30", "Benzene chloride", "Chlorbenzene", "Chlorbenzol", "Chloro-Benzene", "Chlorobenzen", "Chlorobenzol", "Clorobenzene", "MCB", "Mono-Chlorobenzene", "Monochlorbenzene", "Monochlorbenzol", "Monochlorobenzene", "Monoclorobenzene", "PhCl", "Phenyl Chloride", "Tetrosin SP"
CAS Number 108-90-7
Chemical Formula C6H5Cl
Average Molecular Mass 112.56
Monoisotopic Mass 112.01
IUPAC Name chlorobenzene
Traditional Name chlorobenzene
SMILES ClC1=CC=CC=C1
InChI Identifier InChI=1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H
InChI Key InChIKey=MVPPADPHJFYWMZ-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Halobenzenes
Direct Parent Chlorobenzenes
Alternate Parents "Aryl Chlorides", "Organochlorides"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "chlorobenzene", "aryl chloride", "organochloride", "Aromatic Homomonocyclic Compound", "Aryl Halide", "Organohalogen Compound"
Descriptors "an aromatic compound (MetaCyc)", "chlorobenzenes (ChEBI)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Liquid
Appearance Colorless liquid.
Melting Point -45.2°C
Boiling Point 132°C (269.6°F)
Solubility 0.498 mg/mL at 25°C
LogP 2.84
Route of Exposure Oral (L200) ; inhalation (L200)
Mechanism of Toxicity The reactive metabolites of chlorobenzene are believed to bind both liver and kidney proteins, causing direct damage. Chlorobenzene also activates nuclear factor-kappa B (NF-kappa B) and p38 mitogen-activated protein kinase, inducing the release of monocyte chemoattractant protein 1 (MCP-1) by lung epithelial cells, causing an inflammatory reponse. (T36, A141)
Metabolism Chlorobenzene is known to be absorbed via ingestion and inhahation. As it is a lipophilic compound, chlorobenzene distributes preferentially to adipose tissue. It is metabolized by cytochrome P-450 enzymes into its major metabolite 4-chlorocatechol. Unchanged chlorobenzene is exhalted and its metabolites are excreted mainly in the urine. (L200)
Toxicity LD50: 515 mg/kg (Intraperitoneal, Mouse) (T26) LD50: 2290 mg/kg (Oral, Rat) (T26) LD50: 1110 mg/kg (Subcutaneous, Rat) (T26)
Lethal Dose
Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources Chlorobenzene is used as a solvent for some pesticide formulations, to degrease automobile parts, and as a chemical intermediate to make several other chemicals. (L200)
Minimum Risk Level Intermediate Oral: 0.4 mg/kg/day (L134)
Health Effects Effects on the central nervous system from breathing chlorobenzene may include unconsciousness and death. Chronic exposure can cause liver and kidney damage. (L200)
Symptoms Symptoms of chlorobenzene exposure include headaches, nausea, sleepiness, numbness, and vomiting. Effects on the central nervous system from breathing chlorobenzene include unconsciousness, tremors, restlessness, and death. (L200)
Treatment Treatment is mainly symptomatic and supportive. (T36)
DrugBank ID
HMDB ID HMDB41855
PubChem Compound ID 7964
ChEMBL ID CHEMBL16200
ChemSpider ID 7676
KEGG Compound ID C06990
UniProt ID 0
OMIM ID 0
ChEBI ID 28097
BioCyc ID CPD-1125
CTD ID C031294
Stitch ID Chlorobenzene
PDB ID 8CL
ACToR ID 300
Wikipedia Link http://en.wikipedia.org/wiki/Chlorobenzene
Creation Date 2009-03-06 18:58:05
Update Date 2014-12-24 20:21:07