ChemicalBook--->CAS DataBase List--->779345-37-8

779345-37-8

779345-37-8 Structure

779345-37-8 Structure
IdentificationBack Directory
[Name]

5-Fluoro-2-nitropyridine
[CAS]

779345-37-8
[Synonyms]

Pyridine, 5-fluoro-2-nitro-
5-Fluoro-2-nitropyridine ISO 9001:2015 REACH
[Molecular Formula]

C5H3FN2O2
[MDL Number]

MFCD03092917
[MOL File]

779345-37-8.mol
[Molecular Weight]

142.09
Chemical PropertiesBack Directory
[Boiling point ]

245.0±20.0 °C(Predicted)
[density ]

1.439±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,Room Temperature
[form ]

solid
[pka]

-5.01±0.22(Predicted)
[color ]

Light yellow to yellow
[InChI]

InChI=1S/C5H3FN2O2/c6-4-1-2-5(7-3-4)8(9)10/h1-3H
[InChIKey]

CGFYNRVHPARGFY-UHFFFAOYSA-N
[SMILES]

C1([N+]([O-])=O)=NC=C(F)C=C1
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictograms
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P305+P351+P338
[Hazard Codes ]

Xn
[Risk Statements ]

22
[HS Code ]

2933399990
Hazard InformationBack Directory
[Uses]

5-Fluoro-2-nitropyridine is mainly used as a pharmaceutical intermediate. It can be used to prepare substituted heterocyclic compounds with cell proliferation inhibitory activity.
[Synthesis]

2-Amino-5-fluoropyridine

21717-96-4

5-Fluoro-2-nitropyridine

779345-37-8

General procedure for the synthesis of 5-fluoro-2-nitropyridine from 2-amino-5-fluoropyridine: 2-amino-5-fluoropyridine (6.0 g, 53.51 mmol, 1.0 eq.) was dissolved in concentrated H2SO4 (60 ml) and cooled to 0 °C (solution A). In another flask, hydrogen peroxide (13 ml) was slowly added to concentrated sulfuric acid at 0°C (Solution B). Solution A was added dropwise to solution B at 0°C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was poured into ice-cold water and the product was extracted with EtOAc. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give pure 5-fluoro-2-nitropyridine (3.0 g, 39.45% yield). Mass spectrum (electrospray ionization): m/z 142.09 [M + H]+.

[References]

[1] Patent: US2004/209886, 2004, A1
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644
[3] Patent: WO2015/131080, 2015, A1. Location in patent: Paragraph 001083; 001084
[4] Patent: US2010/160340, 2010, A1. Location in patent: Page/Page column 7
[5] Patent: WO2012/97682, 2012, A1. Location in patent: Page/Page column 158
Spectrum DetailBack Directory
[Spectrum Detail]

5-Fluoro-2-nitropyridine(779345-37-8)1HNMR
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