Record Information
Version1.0
Creation date2010-04-08 22:10:23 UTC
Update date2018-05-28 23:39:36 UTC
Primary IDFDB012843
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzene
DescriptionIt is used in processing of modified hop extract Benzene occurs sufficiently often as a component of organic molecules that there is a Unicode symbol in the Miscellaneous Technical block with the code U+232C (?) to represent it with three double bonds, and U+23E3 (?) for a delocalized version.; Benzene, or benzol, is an organic chemical compound the molecular formula C6H6. It is sometimes abbreviated Ph?H. Benzene is a colorless and highly flammable liquid with a sweet smell and a relatively high melting point. Because it is a known carcinogen, its use as an additive in gasoline is now limited, but it is an important industrial solvent and precursor in the production of drugs, plastics, synthetic rubber, and dyes. Benzene is a natural constituent of crude oil, and may be synthesized from other compounds present in petroleum. Benzene is an aromatic hydrocarbon and the second [n]-annulene (-annulene), a cyclic hydrocarbon with a continuous pi bond.; Human exposure to benzene is a global health problem. Benzene targets liver, kidney, lung, heart and the brain and can cause DNA strand breaks, chromosomal damage etc. Benzene causes cancer in both animals and humans. Benzene was first reported to induce cancer in humans in the 1920s. The chemical industry claims it wasn't until 1979 that the cancer inducing properties were determined "conclusively" in humans, despite many references to this fact in the medical literature. Industry exploited this "discrepancy" and tried to discredit animal studies which showed benzene caused cancer saying that they weren't relevant to humans. Benzene has been shown to cause cancer in both sexes of multiple species of laboratory animals exposed via various routes.; In catalytic reforming, a mixture of hydrocarbons with boiling points between 60?200 °C is blended with hydrogen gas and then exposed to a bifunctional platinum chloride or rhenium chloride catalyst at 500?525 °C and pressures ranging from 8?50 atm. Under these conditions, aliphatic hydrocarbons form rings and lose hydrogen to become aromatic hydrocarbons. The aromatic products of the reaction are then separated from the reaction mixture (or reformate) by extraction with any one of a number of solvents, including diethylene glycol or sulfolane, and benzene is then separated from the other aromatics by distillation. The extraction step of aromatics from the reformate is designed to produce aromatics with lowest non-aromatic components. So-called "BTX (Benzene-Toluene-Xylenes)" process consists of such extraction and distillation steps. One such widely used process from UOP was licensed to producers and called the Udex process.; Several tests can determine exposure to benzene. There is a test for measuring benzene in the breath; this test must be done shortly after exposure. Benzene can also be measured in the blood; however, because benzene disappears rapidly from the blood, measurements are accurate only for extremely recent exposures. Benzene exposure should always be minimized.; The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both pure and applied chemistry that in 1890 the German Chemical Society organized an elaborate appreciation in Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper. Here Kekulé spoke of the creation of the theory. He said that he had discovered the ring shape of the benzene molecule after having a reverie or day-dream of a snake seizing its own tail (this is a common symbol in many ancient cultures known as the Ouroboros). This vision, he said, came to him after years of studying the nature of carbon-carbon bonds. This was 7 years after he had solved the problem of how carbon atoms could bond to up to four other atoms at the same time. It is curious that a similar, humorous depiction of benzene had appeared in 1886 in the Berichte der Durstigen Chemischen Gesellschaft (Journal of the Thirsty Chemical Society), a parody of the Berichte der Deutschen Chemischen Gesellschaft, only the parody had monkeys seizing each other in a circle, rather than snakes as in Kekulé's anecdote. Some historians have suggested that the parody was a lampoon of the snake anecdote, possibly already well-known through oral transmission even if it had not yet appeared in print. Others have speculated that Kekulé's story in 1890 was a re-parody of the monkey spoof, and was a mere invention rather than a recollection of an event in his life. Kekulé's 1890 speech in which these anecdotes appeared has been translated into English. If one takes the anecdote as the memory of a real event, circumstances mentioned in the story suggest that it must have happened early in 1862.; Toxic, volatile, flammable liquid hydrocarbon biproduct of coal distillation. Chronic benzene exposure produces hematotoxicity, bone marrow dysplasia (Displasia is a pre-neoplastic or pre-cancerous change). (PMID 16183116). ; It is used as an industrial solvent in paints, varnishes, lacquer thinners, gasoline, etc. Benzene causes central nervous system damage acutely and is carcinogenic. It was formerly used as parasiticide.; Trace amounts of benzene may result whenever carbon-rich materials undergo incomplete combustion. It is produced in volcanoes and forest fires, and is also a component of cigarette smoke. Benzene is a principal component of combustion products produced by the burning of PVC (polyvinyl chloride). Benzene is found in many foods, some of which are safflower, lovage, common bean, and guava.
CAS Number71-43-2
Structure
Thumb
Synonyms
SynonymSource
[6]AnnuleneChEBI
BenzenChEBI
BenzineChEBI
BenzolChEBI
BenzoleChEBI
Bicarburet OF hydrogenChEBI
Coal naphthaChEBI
CyclohexatrieneChEBI
Mineral naphthaChEBI
PheneChEBI
Phenyl hydrideChEBI
PyrobenzolChEBI
PyrobenzoleChEBI
(6)AnnuleneHMDB
AnnuleneHMDB
Aromatic alkaneHMDB
BenzeenHMDB
BenzinHMDB
BenzinumHMDB
Benzol 90HMDB
BenzoleneHMDB
BenzoloHMDB
BenzolumHMDB
BNZHMDB
Carbon oilHMDB
FenzenHMDB
Motor benzolHMDB
PolystreamHMDB
RNGHMDB
{[6]annulene}HMDB
Predicted Properties
PropertyValueSource
Water Solubility1.11 g/LALOGPS
logP2.03ALOGPS
logP1.97ChemAxon
logS-1.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.06 m³·mol⁻¹ChemAxon
Polarizability8.89 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H6
IUPAC namebenzene
InChI IdentifierInChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H
InChI KeyUHOVQNZJYSORNB-UHFFFAOYSA-N
Isomeric SMILESC1=CC=CC=C1
Average Molecular Weight78.1118
Monoisotopic Molecular Weight78.046950192
Classification
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 92.26%; H 7.74%DFC
Melting PointMp 5.53°DFC
Boiling PointBp 80.8° (80.103°, 80.12°, 80.36°, 80.49°)DFC
Experimental Water Solubility1.79 mg/mL at 25 oCMAY,WE et al. (1983)
Experimental logP2.13HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 0.88DFC
Refractive Indexn20D 1.5014DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-70967112fec69784847cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-92ccc664b07cb6c56de9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9000000000-2aae37aac9f2a02d5e8bView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-9100000000-11f8463e7c6286637b1bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-70967112fec69784847cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-92ccc664b07cb6c56de9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9000000000-2aae37aac9f2a02d5e8bView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-004i-9100000000-11f8463e7c6286637b1bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-c5901591488019f3ac5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-004i-9000000000-70967112fec69784847cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-004i-9000000000-92ccc664b07cb6c56de9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-0fb9-9000000000-2aae37aac9f2a02d5e8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (FINNIGAN-MAT 4500) , Positivesplash10-004i-9100000000-11f8463e7c6286637b1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-45ac36cbb443a00d6a17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-9cad19d98e6420c7b6a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-2dace4807cb04a7942deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-b9df9bb9660e1fc49a7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-b9df9bb9660e1fc49a7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b4ff542394722302be43View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-08f396d6cb4660e57caaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID236
ChEMBL IDCHEMBL277500
KEGG Compound IDC01407
Pubchem Compound ID241
Pubchem Substance IDNot Available
ChEBI ID16716
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01505
CRC / DFC (Dictionary of Food Compounds) IDHMJ64-R:HMJ64-R
EAFUS ID300
Dr. Duke IDBENZENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDBNZ
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
larvicideDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).