6-Methylpyridazin-3(2H)-one Chemical Properties

Melting point:

143-145°C

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.51±0.40(Predicted)

form 

powder to crystal

color 

Light yellow to Amber to Dark green

BRN 

109928

InChI

InChI=1S/C5H6N2O/c1-4-2-3-5(8)7-6-4/h2-3H,1H3,(H,7,8)

InChIKey

QZWIXLPWMGHDDD-UHFFFAOYSA-N

SMILES

C1(=O)NN=C(C)C=C1

CAS DataBase Reference

13327-27-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-24/25-37-26

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

6-Methylpyridazin-3(2H)-one Usage And Synthesis

Uses

6-?Methyl-?3-?pyridazinone is a lignin-based dye used on wool. 6-?Methyl-?3-?pyridazinone is also used as a reactant for the synthesis of C-?(1-?aryl-?cyclohexyl)?-?methylamine derivatives as selective, orally available inhibitors of dipeptidyl peptidase IV, imidazopyridazinone derivatives as PDE7 inhibitors and pyridazinone derivatives with an arylpiperazinylalkyl chain as a potentent, orally active, antinociceptive agent.

Definition

ChEBI: 6-Methylpyridazin-3(2H)-one is a member of pyridazines.

Synthesis Reference(s)

Synthesis, p. 1158, 1994 DOI: 10.1055/s-1994-25663

Synthesis

General procedure for the synthesis of 6-methyl-3(2H)-pyridazinone from 4,5-dihydro-6-methylpyridazin-3(2H)-one: bromine (7.68 g, 48.05 mmol) was added slowly and dropwise to a solution of 6-methyl-4,5-dihydropyridazin-3(2H)-one (9.0 g, 80.26 mmol) in acetic acid (90 mL) at 90 °C. The reaction mixture was stirred continuously at 90 °C for 5-6 hours. Upon completion of the reaction, the excess acetic acid was removed by distillation under reduced pressure. The resulting residue was neutralized with aqueous sodium bicarbonate solution, followed by filtration to collect the solid product. The filter cake was dried to give the title compound 6-methyl-3(2H)-pyridazinone (6.0 g, 68% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 12.73 (s, 1H), 7.30 (d, J = 9.6 Hz, 1H), 6.80 (d, J = 9.9 Hz, 1H), 2.14 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6286 - 6291
[2] Journal of Chemical Research, Miniprint, 1995, # 8, p. 1840 - 1852
[3] Journal of the Chemical Society, 1947, p. 239,242
[4] Journal of the Chemical Society, 1947, p. 239,242
[5] Patent: US4595521, 1986, A

6-Methylpyridazin-3(2H)-one(13327-27-0)Related Product Information

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• SULFACHLOROPYRIDAZINE
• Sulfachloropyridazine sodium
• 6-Oxo-1,6-dihydro-pyridazine-3-carboxylicacid
• 4-METHYL-3(2H)-PYRIDAZINONE
• 6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
• 5-Methyl-3(2H)-pyridazinone
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• 6-Methylpyridazin-3(2H)-one
• 2-tert-Butyl-4,5-dichloro-3-2H-pyridazinone
• 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridainone(dl,d-,l-)
• METHYL 1-(2,4-DICHLOROPHENYL)-4-HYDROXY-6-OXO-1,6-DIHYDRO-3-PYRIDAZINECARBOXYLATE
• 6-(2-THIENYL)-3(2H)-PYRIDAZINONE
• 5-ACETYL-4-AMINO-2,6-DIMETHYL-2,3-DIHYDROPYRIDAZIN-3-ONE