Benzoic acid

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Benzoic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Benzoic acid[1]
Systematic IUPAC name
Benzenecarboxylic acid
Other names
  • Carboxybenzene
  • E210
  • Dracylic acid
  • Phenylmethanoic acid
  • Phenylcarboxylic acid
  • Benzoyl alcohol
  • Benzoylic acid
  • Carboxylbenzene
  • Hydrogenphenic acid
  • Phenoic acid
Identifiers
3D model (JSmol)
3DMet
636131
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.562 Edit this at Wikidata
EC Number
  • 200-618-2
E number E210 (preservatives)
2946
KEGG
MeSH benzoic+acid
RTECS number
  • DG0875000
UNII
  • InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) checkY
    Key: WPYMKLBDIGXBTP-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
    Key: WPYMKLBDIGXBTP-UHFFFAOYAD
  • O=C(O)c1ccccc1
Properties
C7H6O2
Molar mass 122.123 g/mol
Appearance Colorless crystalline solid
Odor Faint, pleasant odor
Density 1.2659 g/cm3 (15 °C)
1.0749 g/cm3 (130 °C)[2]
Melting point 122 °C (252 °F; 395 K)[7]
Boiling point 250 °C (482 °F; 523 K)[7]
1.7 g/L (0 °C)
2.7 g/L (18 °C)
3.44 g/L (25 °C)
5.51 g/L (40 °C)
21.45 g/L (75 °C)
56.31 g/L (100 °C)[2][3]
Solubility Soluble in acetone, benzene, CCl4, CHCl3, alcohol, ethyl ether, hexane, phenyls, liquid ammonia, acetates
Solubility in methanol 30 g/100 g (−18 °C)
32.1 g/100 g (−13 °C)
71.5 g/100 g (23 °C)[2]
Solubility in ethanol 25.4 g/100 g (−18 °C)
47.1 g/100 g (15 °C)
52.4 g/100 g (19.2 °C)
55.9 g/100 g (23 °C)[2]
Solubility in acetone 54.2 g/100 g (20 °C)[2]
Solubility in olive oil 4.22 g/100 g (25 °C)[2]
Solubility in 1,4-dioxane 55.3 g/100 g (25 °C)[2]
log P 1.87
Vapor pressure 0.16 Pa (25 °C)
0.19 kPa (100 °C)
22.6 kPa (200 °C)[4]
Acidity (pKa)
−70.28·10−6 cm3/mol
1.5397 (20 °C)
1.504 (132 °C)[2]
Viscosity 1.26 mPa (130 °C)
Structure
Monoclinic
Planar
1.72 D in dioxane
Thermochemistry
146.7 J/mol·K[4]
167.6 J/mol·K[2]
−385.2 kJ/mol[2]
−3228 kJ/mol[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
GHS labelling:
GHS05: CorrosiveGHS08: Health hazard[8]
Danger
H318, H335[8]
P261, P280, P305+P351+P338[8]
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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 121.5 °C (250.7 °F; 394.6 K)[7]
571 °C (1,060 °F; 844 K)[7]
Lethal dose or concentration (LD, LC):
1700 mg/kg (rat, oral)
Safety data sheet (SDS) JT Baker
Related compounds
Other cations
 Sodium benzoate,
Potassium benzoate
Hydroxybenzoic acids
Aminobenzoic acids,
Nitrobenzoic acids,
Phenylacetic acid
Related compounds
 Benzaldehyde,
Benzyl alcohol,
Benzoyl chloride,
Benzylamine,
Benzamide,
Benzonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Benzoic acid (/bɛnˈzoʊ.ɪk/) is a white (or colorless) solid 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 often abbreviated "Bz" (not to be confused with "Bn," which is used for benzyl), thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

Benzoic acid occurs naturally in many plants[9] and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates (/ˈbɛnzoʊ.eɪt/).

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 745. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. ^ a b c d e f g h i j "benzoic acid". chemister.ru. Retrieved 24 October 2018.
  3. ^ Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.
  4. ^ a b c Benzoic acid 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 2014-05-23)
  5. ^ Harris, Daniel (2010). Quantitative Chemical Analysis (8 ed.). New York: W. H. Freeman and Company. pp. AP12. ISBN 9781429254366.
  6. ^ Olmstead, William N.; Bordwell, Frederick G. (1980). "Ion-pair association constants in dimethyl sulfoxide". The Journal of Organic Chemistry. 45 (16): 3299–3305. doi:10.1021/jo01304a033.
  7. ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  8. ^ a b c Sigma-Aldrich Co., Benzoic acid. Retrieved on 2014-05-23.
  9. ^ "Scientists uncover last steps for benzoic acid creation in plants". Purdue Agriculture News.