5-Bromo-2-nitropyridine Chemical Properties

Melting point:

148-150 °C (lit.)

Boiling point:

292.3±20.0 °C(Predicted)

Density 

1.833±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-4.95±0.22(Predicted)

color 

White to yellow to beige powder or crystal or chunks

BRN 

120878

InChI

InChI=1S/C5H3BrN2O2/c6-4-1-2-5(7-3-4)8(9)10/h1-3H

InChIKey

ATXXLNCPVSUCNK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

39856-50-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Bromo-2-nitropyridine Usage And Synthesis

Chemical Properties

Colorless solid

Uses

5-Bromo-2-nitropyridine is employed as a reagent in the synthesis of novel benzinidazoles, potent inhibitors of TIE-2 and VEGFR-2 Tyrosine (T899975) kinase receptors.

Preparation

5-Bromo-2-nitropyridine was prepared from the corresponding amine via hydrogen peroxide oxidation in large scale production. N-Bromosuccinimide (NBS) bromination of 2-aminopyridine in acetonitrile at 0-5 °C delivered 5-bromo-2- aminopyridine with good regioselectivity (>20:1). The brominated amino-pyridine was then reacted with the oxidant mixture, yielding 5-Bromo-2-nitropyridine after dilution with water and isopropanol[1].

Synthesis Reference(s)

[1] Agosti, Alessandro, et al. "Handling Hydrogen Peroxide Oxidations on a Large Scale: Synthesis of 5-Bromo-2-nitropyridine." Organic Process Research & Development 21.3(2017):451-459.

5-Bromo-2-nitropyridine(39856-50-3)Related Product Information

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