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18102

Sigma-Aldrich

Benzoic acid

meets analytical specification of Ph. Eur., BP, USP, FCC, E210, 99.5-100.5% (alkalimetric)

Synonym(s):

Benzenecarboxylic acid, Carboxybenzene

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About This Item

Linear Formula:
C6H5COOH
CAS Number:
65-85-0
Molecular Weight:
122.12
Beilstein:
636131
EC Number:
200-618-2
MDL number:
MFCD00002398
UNSPSC Code:
12352100
PubChem Substance ID:
57647710
NACRES:
NA.21

vapor density

4.21 (vs air)

Quality Level

200

vapor pressure

10 mmHg ( 132 °C)

Assay

99.5-100.5% (alkalimetric)

form

crystalline

autoignition temp.

1061 °F

quality

meets analytical specification of Ph. Eur., BP, USP, FCC, E210

impurities

oxidisable substances, complies
 residual solvents, complies
≤0.0005% heavy metals (as Pb)
≤0.03% halogen compounds (as Cl)
≤0.7% water (Karl Fischer)

ign. residue

≤0.05% (as SO4)

loss

≤0.5% loss on drying, 3 h (via H2SO4)

pH

3-5 (20 °C, 0.1%)

bp

249 °C (lit.)

mp

121-125 °C (lit.)

solubility

water: soluble (2.9 g/l at 25 °C)

cation traces

As: ≤3 mg/kg
Cu: ≤10 mg/kg
Hg: ≤1 mg/kg
Pb: ≤2 mg/kg
Zn: ≤20 mg/kg

suitability

complies for appearance of solution
complies for reaction against H2SO4

SMILES string

OC(=O)c1ccccc1

InChI

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

InChI key

WPYMKLBDIGXBTP-UHFFFAOYSA-N

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General description

Benzoic acid is an aromatic monocarboxylic acid. It occurs in the form of colorless leaflets or needles. It reacts with hydrogenating reagents to afford hexahydrobenzoic acid. On decomposition (by heating) in the presence of lime or alkali, it affords benzene and carbon dioxide. It can be synthesized by the cobalt or manganese catalyzed atmospheric oxidation of toluene.

Application

Benzoic acid may be employed as a standard in the quantitative and calorimetric studies. It may be employed as an intermediate in the synthesis of the following:
  • paints
  • pigments
  • varnish
  • wetting agents
  • aroma compounds
  • benzoyl chloride
  • benzotrichloride
It was used to investigate the mechanism of complex addition reaction of hydroxyl radicals with various aromatic compounds.

Pictograms

Health hazardCorrosion
GHS08,GHS05

Signal Word

Danger

Hazard Statements

H315,H318,H372

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT RE 1 Inhalation

Target Organs

Lungs

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8867
STBK9430
STBK6994
STBK7386
STBG4672V

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Hydroxylation by electrochemically generated OH. radicals. Mono-and polyhydroxylation of benzoic acid: products and isomer distribution.
Oturan MA and Pinson J.
The Journal of Physical Chemistry, 99(38), 13948-13954 (1995)
Eagleson M.
Concise Encyclopedia Chemistry, 122-122 (1994)
Ly Dieu Tran et al.
Journal of the American Chemical Society, 134(44), 18237-18240 (2012-10-30)
An auxiliary-assisted, copper catalyzed or promoted sulfenylation of benzoic acid derivative β-C-H bonds and benzylamine derivative γ-C-H bonds has been developed. The method employs disulfide reagents, copper(II) acetate, and DMSO solvent at 90-130 °C. Application of this methodology to the
Copper-mediated C-H/C-H biaryl coupling of benzoic acid derivatives and 1,3-azoles.
Mayuko Nishino et al.
Angewandte Chemie (International ed. in English), 52(16), 4457-4461 (2013-03-21)
Wanchun Xiang et al.
ChemSusChem, 6(2), 256-260 (2013-01-25)
Sensing the sun: Incorporation of a cyanomethyl benzoic acid electron acceptor into donor-π-acceptor sensitizers for dye-sensitized-solar cell is shown to lead to devices with improved conversion efficiency when compared with more widely used cyanoacetic acid acceptor.
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