6-PHENYL-3(2H)-PYRIDAZINONE Chemical Properties

Melting point:

201-204 °C(lit.)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

11.05±0.40(Predicted)

color 

White to Light yellow

λmax

249nm(HCl aq.)(lit.)

InChI

InChI=1S/C10H8N2O/c13-10-7-6-9(11-12-10)8-4-2-1-3-5-8/h1-7H,(H,12,13)

InChIKey

IJUIPRDMWWBTTQ-UHFFFAOYSA-N

SMILES

C1(=O)NN=C(C2=CC=CC=C2)C=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

6-PHENYL-3(2H)-PYRIDAZINONE Usage And Synthesis

Uses

6-Phenylpyridazin-3(2H)-one is a reagent in the preparation of cyclase activator Runcaciguat, a compound used in the treatment of kidney disease and non-proliferative diabetic retinopathy.

General Description

6-Phenyl-3(2H)-pyridazinone is a pyridazinone derivative that can be prepared from 4,5- dihydro-6-phenyl-3(2H)-pyridazinone. It is reported to be a weak positive inotropic agent. 6-Phenyl-3(2H)-pyridazinone forms the core of compounds that show a potential antiplatelet activity.

Synthesis

The reaction of 19.6 g (162.95 mmol) acetophenone and 5 g (54.32 mmol) oxaloacetic acid monohydrate was stirred at 100 °C for 2 hours. Upon completion of the reaction, the reaction solution was cooled to 40 °C, followed by the addition of 20 mL of water and 4 mL of ammonia. The mixture was extracted twice with 50 mL of dichloromethane. To the resulting aqueous phase, 2.64 mL (53.32 mmol) of hydrazine monohydrate was added, and the reaction was continued with stirring of the mixture at 100 °C for 2 hours. At the end of the reaction, the reaction solution was cooled to room temperature. The precipitated crystals were collected by filtration, washed with water and dried in a vacuum oven at 50 °C overnight. Finally, 4.3 g (24.97 mmol, 15% yield) of 6-phenyl-3-pyridazinone was obtained as colorless crystals.LC-MS (Method 7): Rt = 1.39 min; m/z = 173 (M + H)+. 1H-NMR (400 MHz, DMSO-d6, δ/ppm): 13.2 (s, 1H), 8.04 (d, 1H), 7.86 (d, 2H), 7.53-7.41 (m, 3H), 7.00 (d, 1H).

References

[1] Patent: US2011/34450, 2011, A1. Location in patent: Page/Page column 103
[2] Patent: US2012/28971, 2012, A1. Location in patent: Page/Page column 24-25
[3] Synthesis, 1993, # 3, p. 334 - 342
[4] Medicinal Chemistry Research, 2013, vol. 22, # 6, p. 2553 - 2560
[5] Letters in Drug Design and Discovery, 2013, vol. 10, # 6, p. 507 - 514

6-PHENYL-3(2H)-PYRIDAZINONE(2166-31-6)Related Product Information

• DICLOMEZINE
• Isamfazone
• ZARDAVERINE
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• Chloridazon
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• 4,5-DICHLORO-2-PHENYL-3(2H)-PYRIDAZINONE
• 4-Chloro-5-(methylamino)-2-[3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone,4-chloro-5-(methylamino)-2-(3-(trifluoromethyl)phenyl)-3(2h)-pyridazinon
• 5-BROMO-6-PHENYL-3(2H)-PYRIDAZINONE
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• 4,5-DIBROMO-2-PHENYL-3(2H)-PYRIDAZINONE
• 2,3,4,5-TETRAHYDRO-6-PHENYL-3(2H)-PYRIDAZINONE,4,5-DIHYDRO-6-PHENYL-3(2H)-PYRIDAZINONE
• 5-CHLORO-2-METHYL-6-PHENYL-2,3-DIHYDROPYRIDAZIN-3-ONE
• 6(4-BROMOPHENYL)-3(2H)PYRIDAZINONE
• 6-PHENYL-3(2H)-PYRIDAZINONE-4-CARBOXYLIC ACID ETHYL ESTER
• 6-PHENYL-3(2H)-PYRIDAZINONE
• 6-METHYL-2-PHENYL-3-(2H)-PYRIDAZINONE
• 4-AMINO-6-PHENYL-3(2H)-PYRIDAZINONE