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4-Nitrobenzoic acid

Chemical compound From Wikipedia, the free encyclopedia

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.[5]

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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 Edit this at Wikidata
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 167.120 g·mol−1
Appearance Light yellow crystalline powder[1]
Density 1.58[1]
Melting point 237 °C (459 °F; 510 K)[1]
Boiling point Sublimes[1]
<0.1 g/100 mL at 26 °C [2]
Acidity (pKa) 3.41 (in water),[3] 9.1 (in DMSO)[4]
−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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Production

4-Nitrobenzoic acid is prepared by oxidation of 4-nitrotoluene using oxygen or dichromate as oxidants.[6]

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.[7]

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