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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:13 UTC
Update Date2019-07-23 06:35:08 UTC
HMDB IDHMDB0041855
Secondary Accession Numbers
  • HMDB41855
Metabolite Identification
Common NameChlorobenzene
DescriptionChlorobenzene, also known as benzene chloride or monochlorbenzol, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. Humans may be exposed to this agent via breathing contaminated air (primarily via occupational exposure), consuming contaminated food or water, or by coming into contact with contaminated soil (typically near hazardous waste sites). Chlorobenzene is possibly neutral. Chlorobenzene is a potentially toxic compound. Chlorobenzene is manufactured by chlorination of benzene in the presence of a catalytic amount of Lewis acid such as ferric chloride, sulfur dichloride, and anhydrous aluminium chloride:The catalyst enhances the electrophilicity of the chlorine. These mononitrochlorobenzenes are converted to related 2-nitrophenol, 2-nitroanisole, bis(2-nitrophenyl)disulfide, and 2-nitroaniline by nucleophilic displacement of the chloride, with respectively sodium hydroxide, sodium methoxide, sodium disulfide, and ammonia. In 2015, the SAM science team announced that the Curiosity rover reported evidence of higher concentrations of chlorobenzene in a sedimentary rock, named "Cumberland", on Mars. Industrially the reaction is conducted as a continuous process to minimize the formation of dichlorobenzenes.
Structure
Data?1563863708
Synonyms
ValueSource
Benzene chlorideChEBI
MonochlorbenzolChEBI
MonochlorobenzeneChEBI
PHCLChEBI
Phenyl chlorideChEBI
6-Chlorobenzene-1,2,4-triolHMDB
6-ChlorohydroxyquinolHMDB
Abluton T30HMDB
ChloorbenzeenHMDB
ChlorbenzeneHMDB
ChlorbenzolHMDB
Chloro-benzeneHMDB
ChlorobenzenHMDB
Chlorobenzene (acd/name 4.0)HMDB
ChlorobenzenuHMDB
ChlorobenzolHMDB
Chlorobenzol(dot)HMDB
ClorobenzeneHMDB
IP carrier T 40HMDB
MCBHMDB
mono-ChlorobenzeneHMDB
MonochloorbenzeenHMDB
MonochlorbenzeneHMDB
MonoclorobenzeneHMDB
Tetrosin SPHMDB
Chemical FormulaC6H5Cl
Average Molecular Weight112.557
Monoisotopic Molecular Weight112.007977867
IUPAC Namechlorobenzene
Traditional Namechlorobenzene
CAS Registry Number108-90-7
SMILES
ClC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H5Cl/c7-6-4-2-1-3-5-6/h1-5H
InChI KeyMVPPADPHJFYWMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Industrial application:

Environmental role:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-45.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 mg/mL at 25 °CNot Available
LogP2.84Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP2.78ALOGPS
logP2.58ChemAxon
logS-2.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.86 m³·mol⁻¹ChemAxon
Polarizability11.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fr-9700000000-82e784dca91e262a7e4dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-0c50f1cf42286eb0397eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9500000000-12a9a9ae9833f5dbfa91Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03fr-9700000000-82e784dca91e262a7e4dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-0c50f1cf42286eb0397eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9500000000-12a9a9ae9833f5dbfa91Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-7900000000-f0cb54b4cd19ffd26fcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-6dead520c947adb06d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-6dead520c947adb06d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-f0f0380b80e7b8052a43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-b1fbfe73227c7467ed98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-b1fbfe73227c7467ed98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-3e50515b74111df2adf3Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-6900000000-2d1780378a9603646722Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7676
KEGG Compound IDC06990
BioCyc IDCHLOROBENZENE
BiGG IDNot Available
Wikipedia LinkChlorobenzene
METLIN IDNot Available
PubChem Compound7964
PDB IDNot Available
ChEBI ID28097
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dutkiewicz T, Pacholuk B: [Evaluation of chlorobenzene exposure on the basis of determination of 4-chlorocatechol in urine]. Med Pr. 1980;31(4):289-95. [PubMed:7442536 ]
  2. Cesarone CF, Bolognesi C, Santi L: [Influence of structure and physico-chemical properties of chemical agents in the induction of DNA alterations: nitrochlorobenzenes]. Boll Soc Ital Biol Sper. 1980 Aug 30;56(16):1680-6. [PubMed:7459089 ]
  3. Santilio A, Ziemacki G, Stefanelli P, Dommarco R: Evaluation of nitrobenzenes and chlorobenzenes levels in samples of sediments from Italy: a rapid and simple method by automatic extractor and GC/MS ion trap. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2008 Apr;43(5):437-42. doi: 10.1080/10934520701796150. [PubMed:18324529 ]
  4. MORROW PE, MERCER TT: HYGIENIC GUIDE SERIES. CHLOROBENZENE (MONOCHLOROBENZENE, CHLOROBENZOL, PHENYL CHLORIDE). Am Ind Hyg Assoc J. 1964 Jan-Feb;25:97-9. [PubMed:14110685 ]
  5. ROSENBAUM ND, BLEKH RS, et al.: [The use of chlorobenzene as a solvent from the point of view of industrial hygiene]. Gig Sanit. 1947;12(1):21-4. [PubMed:18863227 ]