3-Nitrobenzoic acid Property

Melting point:

139-141 °C(lit.)

Boiling point:

295.67°C (rough estimate)

Density 

1,494 g/cm³

vapor density 

5.76 (vs air)

vapor pressure 

0.005Pa at 25℃

refractive index 

1.6280 (estimate)

Flash point:

190 °C

storage temp. 

no restrictions.

solubility 

water: soluble3g/L at 25°C

form 

Crystals or Powder

pka

3.47(at 25℃)

color 

Slightly green to light yellow

PH

3 (5g/l, H2O, 20℃)(aqueous suspension)

PH Range

3

Water Solubility 

<0.01 g/100 mL at 18 ºC

Merck 

14,6588

BRN 

908644

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

AFPHTEQTJZKQAQ-UHFFFAOYSA-N

LogP

1.1 at 25℃

CAS DataBase Reference

121-92-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 3-nitro-(121-92-6)

EPA Substance Registry System

m-Nitrobenzoic acid (121-92-6)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37-33-36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

RTECS 

DH5000000

Autoignition Temperature

490 °C

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29163900

Hazardous Substances Data

121-92-6(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

3-Nitrobenzoic acid Chemical Properties,Usage,Production

Chemical Properties

White or light yellow monoclinic leaf-like crystal. Soluble in acetone, chloroform, ethanol and ether, slightly soluble in benzene, water, carbon disulfide and petroleum ether, more soluble in hot water. It smells like almonds. 3-nitrobenzoic acid is quite a strong acid, it is soluble in a relatively weak base. It is about ten times more acidic than benzoic acid.The conjugate base of benzoic acid is stabilised by the presence of the electron withdrawing nitro group which explains its increased acidity in comparison to unsubstituted benzoic acid.

Uses

3-Nitrobenzoic acid was used to investigated the role of ozone as additional decomposition or finishing reagent in the degradation of o-, m- and p-nitobenzoic acids

Application

3-Nitrobenzoic acid is an intermediate of photosensitive materials, functional pigments and drugs. In the pharmaceutical industry, it is used to produce bile acid, acetic acid and so on.
m-nitrobenzoic acid is a reagent used in the coupling of allyl acetate to allylic, aliphatic and benzylic alcohols. It is also used as a chemoattractant against Pseudomonas strains.

Preparation

3-Nitrobenzoic acid is prepared by nitrating benzoic acid at low temperature. Approximately 20% of the 2-nitro isomer and 1.5% of the 4-nitro isomer are co-produced. The 3-nitrobenzoic acid can be purified by recrystallization of the sodium salt. The oxidation of 3-nitrobenzaldehyde, prepared by the controlled oxidation of benzaldehyde, gives a higher yield.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 391, 1941
The Journal of Organic Chemistry, 46, p. 3056, 1981 DOI: 10.1021/jo00328a013

General Description

Off white to yellowish-white crystals. Bitter taste. Melts in hot water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-Nitrobenzoic acid is incompatible with strong oxidizers. 3-Nitrobenzoic acid is also incompatible with strong bases. 3-Nitrobenzoic acid may react with cyanides.

Fire Hazard

Flash point data for 3-Nitrobenzoic acid are not available but 3-Nitrobenzoic acid is probably combustible.

Flammability and Explosibility

Non flammable

Purification Methods

Crystallise the acid from *benzene, H2O, EtOH (charcoal), glacial acetic acid or MeOH/H2O. Dry and store it in a vacuum desiccator. The amide has m 143o (from H2O or *C6H6). [Beilstein 9 III 1489, 9 IV 1055.]