4-Nitrobenzoic acid

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4-Nitrobenzoic acid
4-Nitrobenzoic acid.svg
Names
Preferred IUPAC name
4-Nitrobenzoic acid
Other names
p-Nitrobenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.479
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

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]

Production[edit]

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[edit]

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

References[edit]

  1. ^ "4-nitrobenzoic acid - PubChem Public Chemical Database". Retrieved 11 April 2010.
  2. ^ a b c d "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 (2002). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555.CS1 maint: uses authors parameter (link).
  7. ^ O. Kamm, A. O. Matthews (1922). "p-Nitrobenzoic Acid". Org. Synth. 2: 53. doi:10.15227/orgsyn.002.0053.CS1 maint: uses authors parameter (link)
  8. ^ "Material Safety Data Sheet - P-nitrobenzoic acid MSDS". Retrieved 11 April 2010.