2-BENZYL-4,5-DICHLORO-2,3-DIHYDROPYRIDAZIN-3-ONE Chemical Properties

Melting point:

86 °C(Solv: hexane (110-54-3))

Boiling point:

338.0±52.0 °C(Predicted)

Density 

1.38±0.1 g/cm3(Predicted)

storage temp. 

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

pka

-3.51±0.20(Predicted)

form 

Solid

color 

White to off-white

Safety Information

Hazard Codes 

T

Risk Statements 

25-36

Safety Statements 

26-45

2-BENZYL-4,5-DICHLORO-2,3-DIHYDROPYRIDAZIN-3-ONE Usage And Synthesis

Uses

EcDsbB-IN-9 (Compound 9) is a potent E. coli DsbB (EcDsbB) inhibitor with an IC50 of 1.7 μM and a Ki of 46 nM[1].

Synthesis

To a round bottom flask was added 4,5-dichloropyridazin-3(2H)-one (50 g, 303.03 mmol), N,N-dimethylformamide (DMF, 150 mL), potassium carbonate (K2CO3, 46 g, 333.33 mmol) and benzyl bromide (51.83 g, 303.03 mmol). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction mixture was slowly poured into water (500 mL) and a solid precipitate was precipitated. The suspension was continued to be stirred at room temperature for 1 hour. Subsequently, the solid product was separated by filtration and dried under vacuum to afford 2-benzyl-4,5-dichloropyridazin-3(2H)-one as a tan solid (74 g, 97% yield). The product was analyzed by high performance liquid chromatography (HPLC, Method A) with a retention time of 2.788 min; liquid chromatography-mass spectrometry (LCMS) showed a molecular ion peak (M+1) of 255.1.

References

[1] Landeta C, et al. Compounds targeting disulfide bond forming enzyme DsbB of Gram-negative bacteria. Nat Chem Biol. 2015 Apr;11(4):292-8. DOI:10.1038/nchembio.1752

2-BENZYL-4,5-DICHLORO-2,3-DIHYDROPYRIDAZIN-3-ONE(41933-33-9)Related Product Information

• 4,5-DICHLORO-2-(4-METHYLBENZYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• 2-(2-CHLORO-6-FLUOROBENZYL)-4,5-DICHLOROPYRIDAZINE-3-(2H)-ONE
• AURORA 12480
• 4,5-DICHLORO-2-(2,6-DICHLOROBENZYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• AURORA 12806
• 4,5-DICHLORO-2-(2-FLUOROBENZYL)PYRIDAZINE-3(2H)-ONE
• AURORA 12558
• 4,5-DICHLORO-2-(4-CHLOROBENZYL)-2,3-DIHYDROPYRIDAZIN-3-ONE
• AURORA 12581
• 2-BENZYL-4,5-DICHLORO-2,3-DIHYDROPYRIDAZIN-3-ONE
• AURORA 12539