Pyridazine N-oxide Chemical Properties

Melting point:

298-305 °C

form 

solid

InChI

1S/C4H4N2O/c7-6-4-2-1-3-5-6/h1-4H

InChIKey

GAJBWMUZVXJIBO-UHFFFAOYSA-N

SMILES

[O-][n+]1ccccn1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

RIDADR 

UN 3335

WGK Germany 

3

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3

Pyridazine N-oxide Usage And Synthesis

Uses

Coupling partner in Pd-catalyzed direct arylation reactions.

Synthesis

Pyridazine N-oxide was prepared as follows: appropriate diazine (1 eq.) and mCPBA (1 eq.) were dissolved in DCM (0.2 M). The reaction was stirred for 16 hours. PPh3 (0.5 eq.) was then added to reduce any unreacted peracid and the mixture was stirred for a further 4 hours. The volatiles were evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give pyridazine N-oxide.

Purification Methods

Purify the oxide by distillation in a vacuum and by sublimation in vacuo. When a solution of the oxide in MeOH is treated with an aqueous solution of CuCl2, the [C4H4N2O]2—CuCl2-2H2O-complex (m 182-183o) is formed from which the oxide can be recovered . [Pollak et al. J Org Chem 35 2478 1970, Klinge et al. Recl Trav Chim, Pays Bas 95 21 1976, Ohsawa et al. Tetrahedron Lett 1979 1978, Koelsch & Gumprecht J Org Chem 23 1605 1958, Beilstein 23 III/IV 890.]

Pyridazine N-oxide(1457-42-7)Related Product Information

• Hydralazine
• Sulfachloropyridazine sodium
• SULFACHLOROPYRIDAZINE
• Magnesium oxide
• Thioridazine
• Pyridazine
• Iron oxide
• Pyridaphenthion
• NITRIC OXIDE
• Sulfamethoxypyridazine
• Propylene oxide
• ETHYLENE OXIDE
• Cuprous oxide
• Zinc oxide
• (Diethoxymethyl)diphenylphosphine oxide
• NITROUS OXIDE
• BENZO[C]CINNOLINE N-OXIDE
• 3-METHOXYPYRIDAZINE 1-OXIDE