6-chloro-3-nitroimidazo[1,2-b]pyridazine Chemical Properties

Melting point:

142-145 °C

Density 

1.85±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-1.69±0.30(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C6H3ClN4O2/c7-4-1-2-5-8-3-6(11(12)13)10(5)9-4/h1-3H

InChIKey

IJEZMDPWGDWYKJ-UHFFFAOYSA-N

SMILES

C12=NC=C([N+]([O-])=O)N1N=C(Cl)C=C2

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

F 

10-34

6-chloro-3-nitroimidazo[1,2-b]pyridazine Usage And Synthesis

Synthesis

The general procedure for the synthesis of 6-chloro-3-nitroimidazo[1,2-b]pyridazine from 6-chloroimidazo[1,2-b]pyridazine was as follows: 6-chloroimidazo[1,2-b]pyridazine (4.95 g, 31.6 mmol) was dissolved in 60 mL of concentrated sulfuric acid and cooled in an ice bath. Nitric acid (9.9 mL, 158 mmol) was added slowly and dropwise under stirring conditions. The reaction mixture was stirred at 0 °C for 30 min, followed by continued stirring at room temperature for 4.5 h to ensure complete reaction. Upon completion of the reaction, the mixture was slowly poured into ice water and the resulting aqueous solution was neutralized with 50% aqueous sodium hydroxide. Subsequently, extraction was carried out with ethyl acetate (3 x 400 mL). The organic phases were combined and washed sequentially with water (2 x 400 mL) and saturated saline (400 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the target product 6-chloro-3-nitroimidazo[1,2-b]pyridazine (5.7 g, 91% yield) in the form of light yellow powder.

References

[1] Patent: WO2010/33941, 2010, A1. Location in patent: Page/Page column 35
[2] Patent: CN106632353, 2017, A. Location in patent: Paragraph 0013; 0015; 0017; 0018; 0019; 0020
[3] Patent: WO2009/60197, 2009, A1. Location in patent: Page/Page column 113
[4] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 1, p. 122 - 131
[5] Patent: US2012/65184, 2012, A1. Location in patent: Page/Page column 39

6-chloro-3-nitroimidazo[1,2-b]pyridazine(18087-76-8)Related Product Information

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