Benzoic acid

Benzoic acid
Skeletal formula	Ball-and-stick model
Names
	Preferred IUPAC name Benzoic acid
	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
CAS Number	65-85-0 ;
3D model (JSmol)	Interactive image;
3DMet	B00053;
Beilstein Reference	636131
ChEBI	CHEBI:30746 ;
ChEMBL	ChEMBL541 ;
ChemSpider	238 ;
DrugBank	DB03793 ;
ECHA InfoCard	100.000.562
EC Number	200-618-2;
E number	E210 (preservatives)
Gmelin Reference	2946
KEGG	D00038 ;
MeSH	benzoic+acid
PubChem CID	243;
RTECS number	DG0875000;
UNII	8SKN0B0MIM ;
CompTox Dashboard (EPA)	DTXSID6020143 ;
	InChI InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) Key: WPYMKLBDIGXBTP-UHFFFAOYSA-N ; InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) Key: WPYMKLBDIGXBTP-UHFFFAOYAD;
	SMILES O=C(O)c1ccccc1;
Properties
Chemical formula	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)
Melting point	122 °C (252 °F; 395 K)
Boiling point	250 °C (482 °F; 523 K)
Solubility in water	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)
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)
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)
Solubility in acetone	54.2 g/100 g (20 °C)
Solubility in olive oil	4.22 g/100 g (25 °C)
Solubility in 1,4-dioxane	55.3 g/100 g (25 °C)
log P	1.87
Vapor pressure	0.16 Pa (25 °C); 0.19 kPa (100 °C); 22.6 kPa (200 °C)
Acidity (pKa)	4.202 (H2O); 11.02 (DMSO);
Magnetic susceptibility (χ)	−70.28·10−6 cm3/mol
Refractive index (nD)	1.5397 (20 °C); 1.504 (132 °C)
Viscosity	1.26 mPa (130 °C)
Structure
Crystal structure	Monoclinic
Molecular shape	Planar
Dipole moment	1.72 D in dioxane
Thermochemistry
Heat capacity (C)	146.7 J/mol·K
Std molar; entropy (S⦵298)	167.6 J/mol·K
Std enthalpy of; formation (ΔfH⦵298)	−385.2 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−3228 kJ/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H335
Precautionary statements	P261, P280, P305+P351+P338
NFPA 704 (fire diamond)	2 1 0
Flash point	121.5 °C (250.7 °F; 394.6 K)
Autoignition; temperature	571 °C (1,060 °F; 844 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1700 mg/kg (rat, oral)
Safety data sheet (SDS)	JT Baker
Related compounds
Other cations	Sodium benzoate,; Potassium benzoate
Related carboxylic acids	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). verify (what is ?) Infobox references

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/.

^ 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.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "benzoic acid". chemister.ru. Retrieved 24 October 2018.
^ Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.
^ ^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)
^ Harris, Daniel (2010). Quantitative Chemical Analysis (8 ed.). New York: W. H. Freeman and Company. pp. AP12. ISBN 9781429254366.
^ 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.
^ ^a ^b ^c ^d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ ^a ^b ^c Sigma-Aldrich Co., Benzoic acid. Retrieved on 2014-05-23.
^ "Scientists uncover last steps for benzoic acid creation in plants". Purdue Agriculture News.

[iupac2013-1] 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.

[chemister-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "benzoic acid". chemister.ru. Retrieved 24 October 2018.

[sioc-3] Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.

[nist-4] 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.

[GESTIS-7] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[sigma-8] Sigma-Aldrich Co., Benzoic acid. Retrieved on 2014-05-23.

[9] "Scientists uncover last steps for benzoic acid creation in plants". Purdue Agriculture News.

[1]

[2]

[7]

[3]

[4]

[5]

[6]

[8]

[9]