6-Methylpyridazin-3(2H)-on

Bezeichnung:6-Methylpyridazin-3(2H)-on

CAS-Nr13327-27-0

Englisch Name:6-Methylpyridazin-3(2H)-one

CBNumberCB0463313

SummenformelC5H6N2O

Molgewicht110.11

MOL-Datei13327-27-0.mol

Synonyma

6-Methylpyridazin-3(2H)-on

6-Methylpyridazin-3(2H)-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	143-145°C
Dichte	1.22±0.1 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
Aggregatzustand	powder to crystal
pka	11.51±0.40(Predicted)
Farbe	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 Datenbank	13327-27-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	22-24/25-37-26
WGK Germany	WGK 3
HazardClass	IRRITANT
HS Code	29339900
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

6-Methylpyridazin-3(2H)-one Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Verwenden
6-Methylpyridazin-3(2H)-one is a lignin-based dye used on wool. It 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
Synthese

5157-08-4

13327-27-0

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).
Einzelnachweise
[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] Patent: US4595521, 1986, A

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