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 (JSmol)	Interactive image
ChEBI	CHEBI:262350  Y
ChEMBL	ChEMBL101263  Y
ChemSpider	5882  Y
ECHA InfoCard	100.000.479
PubChem CID	6108
UNII	G83NWR61OW  Y
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) 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]
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). Y  verify  (what is  YN ?) 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 anesthetic 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". Archived from the original on 27 May 2008. 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 (2002). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN   3527306730..
7. O. Kamm; A. O. Matthews (1922). "p-Nitrobenzoic Acid". Org. Synth. 2: 53. doi:10.15227/orgsyn.002.0053.
8. "Material Safety Data Sheet - P-nitrobenzoic acid MSDS". Archived from the original on 7 August 2011. Retrieved 11 April 2010.