4-METHOXYPYRIDAZINE Chemical Properties

Melting point:

43-44℃

Boiling point:

244℃

Density 

1.102

Flash point:

89℃

storage temp. 

Sealed in dry,Room Temperature

pka

4.28±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

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

InChIKey

NSGNREBTEFKPIL-UHFFFAOYSA-N

SMILES

C1=NN=CC=C1OC

Safety Information

HS Code 

2933998090

4-METHOXYPYRIDAZINE Usage And Synthesis

Uses

4-methoxypyridazine can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Uses

To a solution of 3 ,6-dichloro-4- methoxypyridazine (30 g, 167.59 mmol, 1.00 equiv) and ammonium formate (3 1 g, 491.63 mmol, 2.93 equiv) in MeOH (500 mL) was added 10% palladium on carbon (3 g) catalyst. The mixture was stirred under 1 atmosphere of at rt overnight. The catalyst was removed by filtration and the filtrate was concentrated under vacuum. The residue was triturated in 500 mL of DCM MeOH ( 10: 1 ) and the solid material was filtered out. The filtrate was concentrated under vacuum and the residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (2:1 to 1: 1) to give 1 5 g (81%) of 4-methoxypyridazine as a brown oil. TLC: petroleum ether: ethyl acetate=2: 1 , Rf=0.1 .

Synthesis

General procedure for the synthesis of 4-methoxypyridazine from 4-methoxy-3,6-dichloropyridazine: 10% palladium carbon (3 g) catalyst was added to a solution of methanol (500 mL) containing 3,6-dichloro-4-methoxypyridazine (30 g, 167.59 mmol, 1.00 equiv) and ammonium formate (31 g, 491.63 mmol, 2.93 equiv). The reaction mixture was stirred at room temperature and 1 atm overnight. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under vacuum. The concentrated residue was ground in a solvent mixture of dichloromethane and methanol (500 mL, 10:1 v/v) and subsequently filtered to collect the solid. The filtrate was again concentrated under vacuum and the residue was purified by silica gel column chromatography with the eluent being a solvent mixture of ethyl acetate and petroleum ether (the ratio was tapered from 2:1 to 1:1), resulting in 15 g (81% yield) of 4-methoxypyridazine as a brown oil. Thin-layer chromatography (TLC) conditions: the ratio of petroleum ether to ethyl acetate was 2:1, and the Rf value was 0.1.

References

[1] Patent: WO2013/127268, 2013, A1. Location in patent: Page/Page column 99
[2] Helvetica Chimica Acta, 1956, vol. 39, p. 1755,1762

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