4-Fluoronitrobenzene Explained

4-Fluoronitrobenzene is an organic compound with the formula FC6H4NO2. It is one of three isomeric fluoronitrobenzenes.[1] A yellow oil, it is prepared from 4-nitrochlorobenzene using the Halex process:

4-Fluoronitrobenzene can be hydrogenated to give 4-fluoroaniline,[2] which is a precursor to the fungicide fluoroimide.

Owing to the presence of the electron withdrawing nitro group, the fluoride is a good leaving group in fluoronitrobenzenes. Thus reaction with phenoxide gives the mononitrodiphenylether.[3]

References

  1. Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005.
  2. 10.1126/science.1242005 . Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines . 2013 . Jagadeesh . Rajenahally V. . Surkus . Annette-Enrica . Junge . Henrik . Pohl . Marga-Martina . Radnik . Jörg . Rabeah . Jabor . Huan . Heming . Schünemann . Volker . Brückner . Angelika . Beller . Matthias . Science . 342 . 6162 . 1073–1076 . 24288327 . 2013Sci...342.1073J . 11780985 .
  3. 10.15227/orgsyn.014.0066 . p-Nitrodiphenyl Ether . Organic Syntheses . 1934 . 14 . 66. Ray Q.. Brewster. Theodore . Groening .

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