en 4-Fluoronitrobenzene

4-Fluoronitrobenzene
Names
	Other names 1-fluoro-4-nitrobenzene, 1-nitro-4-fluorobenzene
Identifiers
CAS Number	350-46-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL163729;
ChemSpider	13856885;
ECHA InfoCard	100.005.912
EC Number	206-502-8;
PubChem CID	9590;
UNII	A2M2FH7XHH;
CompTox Dashboard (EPA)	DTXSID9022025 ;
	InChI InChI=1S/C6H4FNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H Key: WFQDTOYDVUWQMS-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1[N+](=O)[O-])F;
Properties
Chemical formula	C6H4FNO2
Molar mass	141.101 g·mol−1
Appearance	yellow 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:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H312, H317, H331, H373, H412
Precautionary statements	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). Infobox references

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]

References

^ "1-Fluoro-4-nitrobenzene". pubchem.ncbi.nlm.nih.gov.
^ Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
^ 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.
^ Brewster, Ray Q.; Groening, Theodore (1934). "p-Nitrodiphenyl Ether". Organic Syntheses. 14: 66. doi:10.15227/orgsyn.014.0066.

[1] "1-Fluoro-4-nitrobenzene". pubchem.ncbi.nlm.nih.gov.

[Ullmann-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.

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