4-Fluoronitrobenzene

Last updated
4-Fluoronitrobenzene
4-Fluornitrobenzol.svg
Names
Other names
1-fluoro-4-nitrobenzene, 1-nitro-4-fluorobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.912 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-502-8
PubChem CID
UNII
  • InChI=1S/C6H4FNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H
    Key: WFQDTOYDVUWQMS-UHFFFAOYSA-N
  • C1=CC(=CC=C1[N+](=O)[O-])F
Properties
C6H4FNO2
Molar mass 141.101 g·mol−1
Appearanceyellow solid, melting near room temperature
Density 1.340 g/cm3
Melting point 22–24 °C (72–75 °F; 295–297 K)
Boiling point 206 °C (403 °F; 479 K)
Hazards
GHS labelling: [1]
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H301, H302, H312, H317, H331, H373, H412
P260, P261, P264, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P317, P319, P321, P330, P333+P313, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Fluoronitrobenzene is an organic compound with the formula FC6H4NO2. It is one of three isomeric fluoronitrobenzenes. [2] A yellow oil, it is prepared from 4-nitrochlorobenzene using the Halex process:

O2NC6H4Cl + KF → O2NC6H4F + KCl

4-Fluoronitrobenzene can be hydrogenated to give 4-fluoroaniline, [3] which is a precursor to the fungicide fluoroimide  [ de ] and parafluorofentanyl.

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. [4]

Applications

  1. U-41792
  2. B777-81
  3. WAY-213,613
  4. Butacetin [5]

References

  1. ↑ "1-Fluoro-4-nitrobenzene". pubchem.ncbi.nlm.nih.gov.
  2. ↑ Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi : 10.1002/14356007.a17_411
  3. ↑ Jagadeesh, Rajenahally V.; Surkus, Annette-Enrica; Junge, Henrik; Pohl, Marga-Martina; Radnik, Jörg; Rabeah, Jabor; Huan, Heming; Schünemann, Volker; Brückner, Angelika; Beller, Matthias (2013). "Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines". Science. 342 (6162): 1073–1076. Bibcode:2013Sci...342.1073J. doi:10.1126/science.1242005. PMID   24288327. S2CID   11780985.
  4. ↑ Brewster, Ray Q.; Groening, Theodore (1934). "p-Nitrodiphenyl Ether". Organic Syntheses. 14: 66. doi:10.15227/orgsyn.014.0066.
  5. ↑ Bowden, K.; Green, P. N. (1954). "Syntheses in the piperidine series. Part II. The preparation of pi-peridyl ethers and related compounds". Journal of the Chemical Society (Resumed): 1795. doi:10.1039/jr9540001795.
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