4-Nitrobiphenyl

4-Nitrobiphenyl
Names
	Other names 4-nitro-1,1′-biphenyl
Identifiers
CAS Number	92-93-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82504;
ChEMBL	ChEMBL352531;
ChemSpider	21109008;
DrugBank	DB12300;
ECHA InfoCard	100.002.005
EC Number	202-204-7;
KEGG	C19473;
PubChem CID	7114;
RTECS number	DV5600000;
UNII	QM80NUW6WZ;
UN number	2811
CompTox Dashboard (EPA)	DTXSID9041522 ;
	InChI InChI=1S/C12H9NO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H Key: BAJQRLZAPXASRD-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)C2=CC=C(C=C2)[N+](=O)[O-];
Properties
Chemical formula	C12H9NO2
Molar mass	199.209 g·mol−1
Melting point	114 °C (237 °F; 387 K)
Boiling point	340 °C (644 °F; 613 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Nitrobiphenyl is an organic compound with the formula C₆H₅−C₆H₄NO₂. It is one of three isomers of nitrobiphenyl and probably the most widely used. It is a precursor to the antioxidant 4-aminobiphenyl. 4-Nitrobiphenyl is readily prepared by nitration of biphenyl.^[1] It can also be prepared by cross-coupling reactions.^[2]

4-Nitrobiphenyl is commonly invoked as a pollutant.^[3]^[4]

References

^ Smith, Keith; Musson, Adam; Deboos, Gareth A. (1998). "A Novel Method for the Nitration of Simple Aromatic Compounds". The Journal of Organic Chemistry. 63 (23): 8448–8454. doi:10.1021/jo981557o.
^ Wolfe, John P.; Singer, Robert A.; Yang, Bryant H.; Buchwald, Stephen L. (1999). "Highly Active Palladium Catalysts for Suzuki Coupling Reactions". Journal of the American Chemical Society. 121 (41): 9550–9561. doi:10.1021/ja992130h.
^ Kovacic, Peter; Somanathan, Ratnasamy (2014). "Nitroaromatic compounds: Environmental toxicity, carcinogenicity, mutagenicity, therapy and mechanism". Journal of Applied Toxicology. 34 (8): 810–824. doi:10.1002/jat.2980. PMID 24532466.
^ Fu, Peter P. (1990). "Metabolism of Nitro-Polycyclic Aromatic Hydrocarbons". Drug Metabolism Reviews. 22 (2–3): 209–268. doi:10.3109/03602539009041085. PMID 2272288.