InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)^Y

Key: WPYMKLBDIGXBTP-UHFFFAOYSA-N^Y
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
c1ccc(cc1)C(=O)O

Properties

Chemical formula

C₇H₆O₂

Molar mass

122.12 g·mol⁻¹

Appearance

Colorless crystalline solid

Odor

faint, pleasant odor

Density

1.2659 g/cm³ (15 °C)
1.0749 g/cm³ (130 °C)

Melting point

122.41 °C (252.34 °F; 395.56 K)

Boiling point

249.2 °C (480.6 °F; 522.3 K)
370 °C (698 °F; 643 K)
decomposes

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 (pK_a)

4.202

Magnetic susceptibility (χ)

-70.28·10⁻⁶ cm³/mol

Refractive index (n_D)

1.5397 (20 °C)
1.504 (132 °C)

Viscosity

1.26 mPa (130 °C)

Structure

1.72 D in Dioxane

Thermochemistry

Specific
heat capacity (C)

146.7 J/mol·K

Std molar
entropy (S^o₂₉₈)

167.6 J/mol·K

Std enthalpy of
formation (Δ_fH^o₂₉₈)

-385.2 kJ/mol

Std enthalpy of
combustion (Δ_cH^o₂₉₈)

-3228 kJ/mol

Hazards

Main hazards

Irritant

Danger

GHS hazard statements

H318, H335

GHS precautionary statements

P261, P280, P305+351+338

EU classification (DSD)

R37, R41

S26, S39

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)

Related compounds

Related carboxylic acids

Hydroxybenzoic acids
Aminobenzoic acids,
Nitrobenzoic acids,
Phenylacetic acid

Related compounds

Benzaldehyde,
Benzyl alcohol,
Benzoyl chloride,
Benzylamine,
Benzamide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Benzoic acid /bɛnˈzoʊ.ɪk/, C₇H₆O₂ (or C₆H₅COOH), is a colorless crystalline solid and a simple aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only known source. Benzoic acid occurs naturally in many plants and it serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives and 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/.

Benzoic acid was discovered in the sixteenth century. The dry distillation of gum benzoin was first described by Nostradamus (1556), and then by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).

Pioneer work in 1830 through a variety of experiences based on amygdalin, obtained from bitter almonds (the fruit of Prunus dulcis) oil by Pierre Robiquet and Antoine Boutron-Charlard, two French chemists, had produced benzaldehyde but they failed in working out a proper interpretation of the structure of amygdalin that would account for it, and thus missed the identification of the benzoyl radical C₇H₅O. This last step was achieved some few months later (1832) by Justus von Liebig and Friedrich Wöhler, who determined the composition of benzoic acid. These latter also investigated how hippuric acid is related to benzoic acid.

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Wikipedia