4-Nitrobenzoic acid

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

4-Nitrobenzoic acid
Names
Preferred IUPAC name
4-Nitrobenzoic acid
Other names
p-Nitrobenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.479
UNII
  • InChI=1S/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10) checkY
    Key: OTLNPYWUJOZPPA-UHFFFAOYSA-N checkY
  • InChI=1/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10)
    Key: OTLNPYWUJOZPPA-UHFFFAOYAB
  • O=[N+]([O-])c1ccc(C(=O)O)cc1
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]
-78.81·10−6 cm3/mol
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 °C [77 °F], 100 kPa).
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Infobox references

Production

4-Nitrobenzoic acid is prepared by oxidation of 4-nitrotoluene using oxygen or dichromate as oxidants.[7]

Preparation of 4-Nitrobenzoic acid

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.

Safety

This compound has a rat LD50 of 1960 mg/kg.[8]

References
  1. "4-nitrobenzoic acid - PubChem Public Chemical Database". Retrieved 11 April 2010.
  2. "Safety data for p-nitrobenzoic acid". Archived from the original on 27 May 2008. 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 (2002). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN 3527306730..
  7. O. Kamm; A. O. Matthews (1922). "p-Nitrobenzoic Acid". Org. Synth. 2: 53. doi:10.15227/orgsyn.002.0053.
  8. "Material Safety Data Sheet - P-nitrobenzoic acid MSDS". Archived from the original on 7 August 2011. Retrieved 11 April 2010.
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