2-Fluoronitrobenzene

2-Fluoronitrobenzene
Names
	Preferred IUPAC name 1-Fluoro-2-nitrobenzene
	Other names 2-nitrofluorobenzene
Identifiers
CAS Number	1493-27-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL49252;
ChemSpider	66528;
ECHA InfoCard	100.014.626
EC Number	216-088-0;
PubChem CID	73895;
UNII	9WUK5DS6YX;
CompTox Dashboard (EPA)	DTXSID1061730 ;
	InChI InChI=1S/C6H4FNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H Key: PWKNBLFSJAVFAB-UHFFFAOYSA-N;
	SMILES C1=CC=C(C(=C1)[N+](=O)[O-])F;
Properties
Chemical formula	C6H4FNO2
Molar mass	141.101 g·mol−1
Appearance	colorless liquid
Density	1.3291 g/cm3
Melting point	−6 °C (21 °F; 267 K)
Boiling point	215 °C (419 °F; 488 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Fluoronitrobenzene is an organic compound with the formula FC₆H₄NO₂. It is one of three isomeric fluoronitrobenzenes.^[1] A colorless liquid, it is prepared from 2-nitrochlorobenzene using the Halex process:

O₂NC₆H₄Cl + KF → O₂NC₆H₄F + KCl

Applications

2-Fluoronitrobenzene has application in the synthesis of Amoxapine,^[2] Olanzapine,^[3] an early synthesis of J-113,397, Deschloroclozapine,^[4] and 11-Piperazinyl-dibenz[b,f][1,4]oxazepane [21636-40-8].^[5]

The closely related compound, 2-chloronitrobenzene is used in the synthesis of quetiapine.

References

^ Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
^ Guo Xia, et al. CN103570641 (2014 to Beijing Venturepharm Technology Co Ltd).
^ Jiban K. Chakrabarti, et al., US5229382 (1993 to Lilly Industries Ltd).
^ Thomas Daniel Aicher, et al. WO2003082877 (Eli Lilly and Co). See ex. 553, 554 & 582.
^ Jain, Manoj S.; Surana, Sanjay J. (2017). "Synthesis and evaluation of antipsychotic activity of 11-(4′-(N-aryl carboxamido/N-aryl-α-phenyl-acetamido)-piperazinyl)-dibenz[b,f][1,4]-oxazepine derivatives". Arabian Journal of Chemistry. 10: S2032–S2039. doi:10.1016/j.arabjc.2013.07.033.

[Ullmann-1] Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411

[2] Guo Xia, et al. CN103570641 (2014 to Beijing Venturepharm Technology Co Ltd).

[3] Jiban K. Chakrabarti, et al., US5229382 (1993 to Lilly Industries Ltd).

[4] Thomas Daniel Aicher, et al. WO2003082877 (Eli Lilly and Co). See ex. 553, 554 & 582.

[5] Jain, Manoj S.; Surana, Sanjay J. (2017). "Synthesis and evaluation of antipsychotic activity of 11-(4′-(N-aryl carboxamido/N-aryl-α-phenyl-acetamido)-piperazinyl)-dibenz[b,f][1,4]-oxazepine derivatives". Arabian Journal of Chemistry. 10: S2032–S2039. doi:10.1016/j.arabjc.2013.07.033.

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