| Identification | Back Directory | [Name]
6-PHENYL-3(2H)-PYRIDAZINONE | [CAS]
2166-31-6 | [Synonyms]
IFLAB-BB F0921-7014
3-Phenyl-6-pyridazinone
3-phenyl-1H-pyridazin-6-one
6-PHENYL-3(2H)-PYRIDAZINONE
6-phenylpyridazin-3(2H)-one
6-Phenyl-2H-pyridazin-3-one
3-Hydroxy-6-phenylpyridazine
3(2H)-Pyridazinone, 6-phenyl-
6-Phenyl-3(2H)-pyridazinone>
6-Phenyl-3(2H)-pyridazinone
6-Phenyl-2,3-dihydropyridazine-3-one
JR-8471, 6-Phenyl-3-(2H)-pyridazinone, 97%
6-PHENYL-3(2H)-PYRIDAZINONE ISO 9001：2015 REACH
8-(2-hydroxypropan-2-yl)-2-furo[2,3-h][1]benzopyranone
2,3-Dihydro-3-oxo-6-phenylpyridazine, (6-Oxo-1,6-dihydropyridazin-3-yl)benzene | [EINECS(EC#)]
218-505-1 | [Molecular Formula]
C10H8N2O | [MDL Number]
MFCD00114953 | [MOL File]
2166-31-6.mol | [Molecular Weight]
172.18 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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