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4-Nitrobiphenyl

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4-Nitrobiphenyl
Names
Other names
4-nitro-1,1′-biphenyl
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.005 Edit this at Wikidata
EC Number
  • 202-204-7
KEGG
RTECS number
  • DV5600000
UNII
UN number 2811
  • 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
  • C1=CC=C(C=C1)C2=CC=C(C=C2)[N+](=O)[O-]
Properties
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).

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

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  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ Fu, Peter P. (1990). "Metabolism of Nitro-Polycyclic Aromatic Hydrocarbons". Drug Metabolism Reviews. 22 (2–3): 209–268. doi:10.3109/03602539009041085. PMID 2272288.