5-Bromo-3-nitropyridine-2-carbonitrile Chemical Properties

Melting point:

101-106 °C

Boiling point:

348.9±42.0 °C(Predicted)

Density 

1.92±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-6.71±0.20(Predicted)

form 

powder to crystal

color 

Light orange to Yellow to Green

InChI

InChI=1S/C6H2BrN3O2/c7-4-1-6(10(11)12)5(2-8)9-3-4/h1,3H

InChIKey

OBVYONPVHIOJJZ-UHFFFAOYSA-N

SMILES

C1(C#N)=NC=C(Br)C=C1[N+]([O-])=O

CAS DataBase Reference

573675-25-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

20/21-25-37/38-41

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29333990

5-Bromo-3-nitropyridine-2-carbonitrile Usage And Synthesis

Chemical Properties

Yellow to light yellow crystals

Uses

Used as an intermediate in organic synthesis.

Synthesis

To a stirred solution of 2,5-dibromo-3-nitro-pyridine (25 g, 88.68 mmol) in propionitrile (100 ml) was added CuCN (8.7 g, 97.55 mmol) and the mixture was heated to 90°C. for 17 h. Then it was allowed to cool to room temperature, diluted with EtOAc, washed twice with brine, dried with Na2SO4 and concentrated. The remaining residue was purified by chromatography (silica gel; DCM/MeOH 95:5- 85:15) to obtain 5-Bromo-3-nitropyridine-2-carbonitrile. Yellow solid, yield 17.5 g, 68%.

References

[1] Patent: EP1757594, 2007, A1. Location in patent: Page/Page column 76
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3608 - 3612
[3] Patent: WO2005/42498, 2005, A2. Location in patent: Page/Page column 43; 44
[4] Patent: WO2006/52514, 2006, A1. Location in patent: Page/Page column 7-8
[5] Patent: WO2006/132837, 2006, A1. Location in patent: Page/Page column 19

5-Bromo-3-nitropyridine-2-carbonitrile(573675-25-9)Related Product Information

• 3-CYANO-5-METHYLPYRIDINE
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• Sodium cyanoborohydride
• 2-Chloro-3-cyanopyridine
• 5-Bromo-2-pyridinecarbonitrile
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• 5-Bromo-2-chloro-3-nitropyridine
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• Methylene dithiocyanate
• 2-Cyano-5-nitropyridine
• 2-Cyano-3-fluoropyridine
• 5-bromo-3-methylpicolinonitrile
• 2-Cyano-3-chloropyridine
• 2-Cyano-3,5-difluoropyridine
• 3-bromo-5-chloropyridine-2-carbonitrile
• 5-Bromo-3-fluoro-pyridine-2-carbonitrile
• 3,5-Dichloro-2-cyanopyridine