4-Nitrobenzoic acid

4-Nitrobenzoic acid
IUPAC name 4-nitrobenzoic acid
Other names p-nitrobenzoic acid
Identifiers
CAS number	62-23-7 Y
PubChem	6108
ChemSpider	5882 Y
ChEBI	CHEBI:262350 Y
ChEMBL	CHEMBL101263 Y
Jmol-3D images	{{#if:O=[N+]([O-])c1ccc(C(=O)O)cc1|Image 1
SMILES O=[N+]([O-])c1ccc(C(=O)O)cc1
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
Properties
Molecular formula	C7H5NO4
Molar mass	167.1189 g/mol[1]
Appearance	Light yellow crystalline powder[2]
Density	1.58[2]
Melting point	237 °C[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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

4-Nitrobenzoic acid is an organic compound with the formula C₆H₄(NO₂)CO₂H. 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]

4-Nitrobenzoic acid is prepared by oxidation of 4-nitrotoluene using oxygen or nitric acid as oxidants. 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.

COSMO Surface of 4-nitrobenzoic acid

Safety

This compound has a rat LD₅₀ of 1960 mg/kg.^[7]

References

1. ↑ "4-nitrobenzoic acid - PubChem Public Chemical Database". Retrieved 11 April 2010. 
2. ↑ 2.0 2.1 2.2 2.3 "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. ↑ "Material Safety Data Sheet - P-nitrobenzoic acid MSDS". Retrieved 11 April 2010.