4-Nitrobenzoic acid

4-Nitrobenzoic acid

Names
Preferred IUPAC name 4-Nitrobenzoic acid
Other names p-Nitrobenzoic acid
Identifiers
CAS Number	62-23-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:262350 Y
ChEMBL	ChEMBL101263 Y
ChemSpider	5882 Y
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) Y Key: OTLNPYWUJOZPPA-UHFFFAOYSA-N Y 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. 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. ↑ 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.