4-Nitrobenzoic acid Property

Melting point:

237-240 °C(lit.)

Boiling point:

295.67°C (rough estimate)

Density 

1.61

refractive index 

1.6280 (estimate)

Flash point:

237 °C

storage temp. 

Store below +30°C.

solubility 

0.42g/l

pka

3.41(at 25℃)

form 

Crystalline Powder

color 

Light yellow

PH

3.1 (0.42g/l, H2O, 20℃)(saturated solution)

Water Solubility 

<0.1 g/100 mL at 26 ºC

Merck 

14,6589

BRN 

973593

Specific Activity

50-60 mCi/mmol

Concentration

0.1 mCi/ml

Solvent

Ethanol

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, cyanides, strong bases.

InChIKey

OTLNPYWUJOZPPA-UHFFFAOYSA-N

LogP

1.890

CAS DataBase Reference

62-23-7(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-nitro-(62-23-7)

EPA Substance Registry System

p-Nitrobenzoic acid (62-23-7)

Safety

Hazard Codes 

Xn

Risk Statements 

22-41-36

Safety Statements 

26-39-24/25

WGK Germany 

1

RTECS 

DH5075000

TSCA 

Yes

HS Code 

29163900

Hazardous Substances Data

62-23-7(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 1960 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H341Suspected of causing genetic defects

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P308+P313IF exposed or concerned: Get medical advice/attention.

4-Nitrobenzoic acid Chemical Properties,Usage,Production

Chemical Properties

light yellow crystalline powder

Uses

4-Nitrobenzoic Acid is used in the synthesis of anti-Trypanosoma cruzi agents in the treatment of chagas disease.

Production Methods

p-Nitrobenzoic acid is produced commercially by the oxidation of 4-nitrotoluene with molecular oxygen. Oxidation with 15 % nitric acid at 175 ℃ produces the acid in 88.5 % yield. An interesting method involves the nitration and subsequent oxidation of polystyrene. This method uses the steric hindrance of the polymer chain to improve the para to ortho ratio of the product.

Definition

ChEBI: A nitrobenzoic acid having the nitro group at the 4-position.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 2387, 1985 DOI: 10.1016/S0040-4039(00)94834-2
Journal of the American Chemical Society, 72, p. 5012, 1950 DOI: 10.1021/ja01167a051

General Description

Odorless pale yellow crystals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

p-Nitrobenzoic acid is incompatible with strong oxidizers. p-Nitrobenzoic acid is also incompatible with strong bases (potassium hydroxide). p-Nitrobenzoic acid may react with cyanides.

Fire Hazard

p-Nitrobenzoic acid is combustible.

Toxicology

Among various nitroaromatics, 4-nitrobenzoic acid (4-NBA) is one of the simplest and basic derivates of the explosives. Moreover, 4-NBA harms human health and causes severe water and atmosphere pollution. 4-Nitrobenzoic acid is stable, toxic, and non-biodegradable. US/Zn0 was found to degrade more than 85% of 4-nitrobenzoic acid in 30 min. There was an apparent synergistic effect between ultrasound and Zn[1-2].

Purification Methods

Purify it as for 3-nitrobenzoic acid above. The amide has m 201.6o (from H2O). [Beilstein 9 III 1537, 9 IV 1072.]

References

[1] Shan Chong. “Ultrasound/Zn0 for aqueous 4-nitrobenzoic acid degradation.” Desalination and Water Treatment 322 1 (2016): 24990–24998.
[2] Xue-Huan Xin . “A luminescent barium-based metal-organic framework: Synthesis, structure and efficient detection of 4-nitrobenzoic acid.” Inorganic Chemistry Communications 97 (2018): Pages 129-133.