4-Nitrobenzoic acid

4-Nitrobenzoic acid

Names
Preferred IUPAC name 4-Nitrobenzoic acid
Other names p-Nitrobenzoic acid
Identifiers
CAS Number	62-23-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:262350
ChEMBL	ChEMBL101263
ChemSpider	5882
ECHA InfoCard	100.000.479
PubChem	6108
InChI InChI=1S/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10) Key: OTLNPYWUJOZPPA-UHFFFAOYSA-N InChI=1/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10) Key: OTLNPYWUJOZPPA-UHFFFAOYAB
SMILES O=[N+]([O-])c1ccc(C(=O)O)cc1
Properties
Chemical formula	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]
Solubility in water	<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 °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 anestheic Procaine and folic acid. It is also a precursor to 4-aminobenzoic acid.^[6]

Production

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

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". 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. O. Kamm and A. O. Matthews "p-Nitrobenzoic Acid" Org. Synth. 1922, volume 2, p. 53. doi:10.15227/orgsyn.002.0053
8. "Material Safety Data Sheet - P-nitrobenzoic acid MSDS". Retrieved 11 April 2010.