4-Nitrobenzoic acid

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]

4-Nitrobenzoic acid

Names
Preferred IUPAC name 4-Nitrobenzoic acid
Other names p-Nitrobenzoic acid
Identifiers
CAS Number	62-23-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:262350
ChEMBL	ChEMBL101263
ChemSpider	5882
ECHA InfoCard	100.000.479
PubChem CID	6108
UNII	G83NWR61OW
CompTox Dashboard (EPA)	DTXSID3020966
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]
Magnetic susceptibility (χ)	-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).  verify (what is  ?) Infobox references

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.

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