4-Nitrobenzoic acid

4-Nitrobenzoic acid
Names
IUPAC name
4-nitrobenzoic acid
Other names
p-nitrobenzoic acid
Identifiers
62-23-7 YesY
ChEBI CHEBI:262350 YesY
ChEMBL ChEMBL101263 YesY
ChemSpider 5882 YesY
Jmol interactive 3D 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 Â°C (459 Â°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 otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°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. 1 2 3 4 "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.
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