6-Chloroimidazo[2,1-f]pyridazine Chemical Properties

Melting point:

114.0 to 118.0 °C

Density 

1.51±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.68±0.30(Predicted)

color 

White to Gray to Brown

InChI

InChI=1S/C6H4ClN3/c7-5-1-2-6-8-3-4-10(6)9-5/h1-4H

InChIKey

MPZDNIJHHXRTIQ-UHFFFAOYSA-N

SMILES

C12=NC=CN1N=C(Cl)C=C2

CAS DataBase Reference

6775-78-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

36/37/39

HazardClass 

IRRITANT

HS Code 

2933599590

6-Chloroimidazo[2,1-f]pyridazine Usage And Synthesis

Physical State

White to Gray to Brown powder to crystal

Uses

6-chloroimidazo[1,2-b]pyridazine (cas# 6775-78-6) is a useful research chemical.

Safe handling

Handling is performed in a well ventilated place.Wear suitable protective equipment.Prevent dispersion of dust.Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Avoid contact with skin,eyes and clothing.

Synthesis

General procedure for the preparation of 6-chloroimidazo[1,2-b]pyridazine: Bromoacetaldehyde diethyl acetal (13.7 g, 69.5 mmol, 1.8 eq.) was added to hydrobromic acid (4.0 mL) and heated to reflux for 1.5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into an isopropanol reaction flask containing an excess of sodium bicarbonate. After stirring for 3 minutes, filtration was performed. To the filtrate was added 3-amino-6-chloropyridazine (5.0 g, 38.6 mmol, 1.0 eq.) and the reflux was continued by heating for 2 hours. At the end of the reaction, the reaction mixture was quenched with water and extracted with ethyl acetate. Finally, the product was purified by column chromatography to give 5.1 g of brown solid in 86% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.89 (s, 1H), 7.88 (d, J = 9.3 Hz, 1H), 7.74 (s, 1H), 7.01 (d, J = 9.3 Hz, 1H).

References

[1] Patent: US2014/256733, 2014, A1. Location in patent: Paragraph 0227-0229
[2] Patent: WO2012/69202, 2012, A1. Location in patent: Page/Page column 46
[3] Patent: EP2463289, 2012, A1. Location in patent: Page/Page column 17-18
[4] Patent: EP2818471, 2014, A1. Location in patent: Paragraph 0117; 0118
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2789 - 2798

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