4-Nitrobenzoic acid

4-Nitrobenzoic acid
Names
IUPAC name
4-nitrobenzoic acid
Other names
p-nitrobenzoic acid
Identifiers
62-23-7 Yes
ChEBI CHEBI:262350 Yes
ChEMBL ChEMBL101263 Yes
ChemSpider 5882 Yes
Jmol-3D images Image
PubChem 6108
Properties
C7H5NO4
Molar mass 167.1189 g/mol[1]
Appearance Light yellow crystalline powder[2]
Density 1.58[2]
Melting point 237 °C (459 °F; 510 K)[2]
Boiling point Sublimes[2]
<0.1 g/100 mL at 26 °C [3]
Acidity (pKa) 3.41 (in water),[4] 9.1 (in DMSO)[5]
Related compounds
Related compounds
Benzoic acid
Nitrobenzene
Anthranilic acid
3,5-Dinitrobenzoic acid, 3-Nitrobenzoic acid, 2-Nitrobenzoic acid
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

4-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is a precursor to 4-nitrobenzoyl chloride, the precursor to the anestheic Procaine and folic acid. It is also a precursor to 4-aminobenzoic acid.[6]

4-Nitrobenzoic acid is prepared by oxidation of 4-nitrotoluene using oxygen or nitric acid as oxidants. Alternatively, it has been prepared by nitration of polystyrene followed by oxidation of the alkyl substituent. This method proceeds with improved para/ortho selectivity owing to the steric protection of the ortho positions by the polymer backbone.

COSMO Surface of 4-nitrobenzoic acid

Safety

This compound has a rat LD50 of 1960 mg/kg.[7]

References

  1. "4-nitrobenzoic acid - PubChem Public Chemical Database". Retrieved 11 April 2010.
  2. 2.0 2.1 2.2 2.3 "Safety data for p-nitrobenzoic acid". Retrieved 11 April 2010.
  3. "p-Nitrobenzoic acid". Archived from the original on 7 May 2010. Retrieved 11 April 2010.
  4. "Dissociation Constants Of Organic Acids And Bases". Retrieved 11 April 2010.
  5. "Bordwell pKa Table (Acidity in DMSO)". Retrieved 11 April 2010.
  6. Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_555.
  7. "Material Safety Data Sheet - P-nitrobenzoic acid MSDS". Retrieved 11 April 2010.