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Benzene information


This article is about the chemical compound. For other uses, see Benzene (disambiguation).
Not to be confused with Petroleum benzine.
Benzene
Benzene molecule
Space-filling model
Skeletal formula detail of benzene.
Skeletal formula detail of benzene.
Geometry
Benzene ball-and-stick model
Benzene ball-and-stick model
Ball and stick model
Sample of benzene
Benzene at room temperature
Names
Preferred IUPAC name
Benzene[1]
Other names
Benzol (historic/German)
Phenane
Phenylene hydride
Cyclohexa-1,3,5-triene; 1,3,5-Cyclohexatriene (theoretical resonance isomers)
[6]Annulene (not recommended[1])
Phene (historic)
Identifiers
CAS Number
  • 71-43-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16716 checkY
ChEMBL
  • ChEMBL277500 checkY
ChemSpider
  • 236 checkY
ECHA InfoCard 100.000.685 Edit this at Wikidata
EC Number
  • 200-753-7
KEGG
  • C01407 checkY
PubChem CID
  • 241
RTECS number
  • CY1400000
UNII
  • J64922108F checkY
CompTox Dashboard (EPA)
  • DTXSID3039242 Edit this at Wikidata
InChI
  • InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H checkY
    Key: UHOVQNZJYSORNB-UHFFFAOYSA-N checkY
SMILES
  • c1ccccc1
Properties
Chemical formula
 C6H6
Molar mass 78.114 g·mol−1
Appearance Colorless liquid
Odor sweet aromatic
Density 0.8765(20) g/cm3[2]
Melting point 5.53 °C (41.95 °F; 278.68 K)
Boiling point 80.1 °C (176.2 °F; 353.2 K)
Solubility in water
 1.53 g/L (0 °C)
1.81 g/L (9 °C)
1.79 g/L (15 °C)[3][4][5]
1.84 g/L (30 °C)
2.26 g/L (61 °C)
3.94 g/L (100 °C)
21.7 g/kg (200 °C, 6.5 MPa)
17.8 g/kg (200 °C, 40 MPa)[6]
Solubility Soluble in alcohol, CHCl3, CCl4, diethyl ether, acetone, acetic acid[6]
Solubility in ethanediol 5.83 g/100 g (20 °C)
6.61 g/100 g (40 °C)
7.61 g/100 g (60 °C)[6]
Solubility in ethanol 20 °C, solution in ethanol:
1.2 mL/L (20% v/v)[7]
Solubility in acetone 20 °C, solution in acetone:
7.69 mL/L (38.46% v/v)
49.4 mL/L (62.5% v/v)[7]
Solubility in diethylene glycol 52 g/100 g (20 °C)[6]
log P 2.13
Vapor pressure 12.7 kPa (25 °C)
24.4 kPa (40 °C)
181 kPa (100 °C)[8]
Conjugate acid Benzenium[9]
Conjugate base Benzenide[10]
UV-vis (λmax) 255 nm
Magnetic susceptibility (χ)
 −54.8·10−6 cm3/mol
Refractive index (nD)
 1.5011 (20 °C)
1.4948 (30 °C)[6]
Viscosity 0.7528 cP (10 °C)
0.6076 cP (25 °C)
0.4965 cP (40 °C)
0.3075 cP (80 °C)
Structure
Molecular shape
 Trigonal planar
Dipole moment
 0 D
Thermochemistry
Heat capacity (C)
 134.8 J/mol·K
Std molar
entropy (S⦵298)
 173.26 J/mol·K[8]
Std enthalpy of
formation (ΔfH⦵298)
 48.7 kJ/mol
Std enthalpy of
combustion (ΔcH⦵298)
 -3267.6 kJ/mol[8]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 potential occupational carcinogen, flammable
GHS labelling:
Pictograms
 GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard[11]
Signal word
 Danger
Hazard statements
 H225, H302, H304, H305, H315, H319, H340, H350, H372, H410[11]
Precautionary statements
 P201, P210, P301+P310, P305+P351+P338, P308+P313, P331[11]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point −11.63 °C (11.07 °F; 261.52 K)
Autoignition
temperature
 497.78 °C (928.00 °F; 770.93 K)
Explosive limits 1.2–7.8%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 930 mg/kg (rat, oral)[13]
LCLo (lowest published)
 44,000 ppm (rabbit, 30 min)
44,923 ppm (dog)
52,308 ppm (cat)
20,000 ppm (human, 5 min)[14]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 1 ppm, ST 5 ppm[12]
REL (Recommended)
 Ca TWA 0.1 ppm ST 1 ppm[12]
IDLH (Immediate danger)
 500 ppm[12]
Safety data sheet (SDS) HMDB
Related compounds
Related compounds
 Toluene
Borazine
Divinylacetylene(isomer)
Dewar benzene(isomer)
Supplementary data page
Benzene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a precursor to the manufacture of chemicals with more complex structures, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major industrial chemical, it finds limited use in consumer items because of its toxicity. Benzene is a volatile organic compound.[15]

Benzene is classified as a carcinogen.

  1. ^ a b Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. pp. 10, 22, 204, 494, 577. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
  3. ^ Arnold, D.; Plank, C.; Erickson, E.; Pike, F. (1958). "Solubility of Benzene in Water". Industrial & Engineering Chemistry Chemical & Engineering Data Series. 3 (2): 253–256. doi:10.1021/i460004a016.
  4. ^ Breslow, R.; Guo, T. (1990). "Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers". Proceedings of the National Academy of Sciences of the United States of America. 87 (1): 167–9. Bibcode:1990PNAS...87..167B. doi:10.1073/pnas.87.1.167. PMC 53221. PMID 2153285.
  5. ^ Coker, A. Kayode; Ludwig, Ernest E. (2007). Ludwig's Applied Process Design for Chemical And Petrochemical Plants. Vol. 1. Elsevier. p. 114. ISBN 978-0-7506-7766-0. Archived from the original on 2016-03-12. Retrieved 2012-05-31.
  6. ^ a b c d e "Benzol". Archived from the original on 2014-05-29. Retrieved 2014-05-29.
  7. ^ a b Atherton Seidell; William F. Linke (1952). Solubilities of Inorganic and Organic Compounds: A Compilation of Solubility Data from the Periodical Literature. Supplement. Van Nostrand. Archived from the original on 2020-03-11. Retrieved 2015-06-27.
  8. ^ a b c Benzene in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-29)
  9. ^ "Benzenium (CID 12533897". PubChem. February 8, 2007. Retrieved September 18, 2022.
  10. ^ "Benzenide (CID 5150480)". PubChem. June 24, 2005. Retrieved September 18, 2022.
  11. ^ a b c Sigma-Aldrich Co., Benzene Archived 2016-12-01 at the Wayback Machine. Retrieved on 2014-05-29.
  12. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0049". National Institute for Occupational Safety and Health (NIOSH).
  13. ^ MSDS
  14. ^ "Benzene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  15. ^ "Benzene fact sheet". CDC. 2 September 2021. Retrieved 16 Aug 2023.

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Benzene

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Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal...

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Aromatic compound

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arenes usually refers to organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past...

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Toluene

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with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group...

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Aromaticity

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other. This commonly seen model of aromatic rings, namely the idea that benzene was formed from a six-membered carbon ring with alternating single and...

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Phenol

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Schotten–Baumann reaction: C6H5COCl + HOC6H5 → C6H5CO2C6H5 + HCl Phenol is reduced to benzene when it is distilled with zinc dust or when its vapour is passed over granules...

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Borazine

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isoelectronic and isostructural with benzene. For this reason borazine is sometimes referred to as “inorganic benzene”. Like benzene, borazine is a colourless liquid...

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Cyclohexane

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hydrogenation of benzene in the presence of a Raney nickel catalyst. Producers of cyclohexane account for approximately 11.4% of global demand for benzene. The reaction...

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Dewar benzene

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Dewar benzene (also spelled dewarbenzene) or bicyclo[2.2.0]hexa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C6H6. The compound...

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Hydroquinone

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Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical...

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Benzene in soft drinks

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Benzene in soft drinks is of potential concern due to the carcinogenic nature of the molecule. This contamination is a public health concern and has caused...

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Benzene hexachloride

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Benzene hexachloride may refer to: Hexachlorocyclohexane Lindane, its gamma isomer, an insecticide Hexachlorobenzene, a fungicide This set index article...

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Phenyl group

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by the symbol Ph. The phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other...

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Benzaldehyde

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Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and...

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Styrene

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C6H5CH=CH2. Its structure consists of a vinyl group as substituent on benzene. Styrene is a colorless, oily liquid, although aged samples can appear...

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Benzoic acid

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organic compound with the formula C6H5COOH, whose structure consists of a benzene ring (C6H6) with a carboxyl (−C(=O)OH) substituent. The benzoyl group is...

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Petrochemical

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are olefins (including ethylene and propylene) and aromatics (including benzene, toluene and xylene isomers). Oil refineries produce olefins and aromatics...

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Isophthalic acid

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Isophthalic acid Names Preferred IUPAC name Benzene-1,3-dicarboxylic acid Other names Isophthalic acid meta-Phthalic acid Identifiers CAS Number 121-91-5 Y...

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Hydrocarbon

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can be gases (such as methane and propane), liquids (such as hexane and benzene), low melting solids (such as paraffin wax and naphthalene) or polymers...

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Methyl phenylacetate

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IUPAC name Methyl phenylacetate Other names Methyl 2-phenylacetate Methyl benzene acetate Identifiers CAS Number 101-41-7 Y 3D model (JSmol) Interactive...

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Locomotive

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sub-categorised by their transmission type. Benzene locomotives have an internal combustion engines that use benzene as fuel. Between the late 1890's and 1900's...

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Mellitic acid

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central benzene ring. The molecule adopts a propeller-like conformation in which the tilt of each carboxylic acid group relative to the central benzene ring...

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