5754-18-7

Basic information

• Product Name: 3,6-Dihydroxy-4-methylpyridazine
• Synonyms: BUTTPARK 47\04-23;4-METHYLPYRIDAZINE-3,6-DIOL;3,6-DIHYDROXY-4-METHYLPYRIDAZINE;CITRACONIC HYDRAZIDE;3,6-DIHYDROXY-4-METHYLPYRIDAZINE (4-METHYLMALEIC HYDRAZIDE);1,2-Dihydro-4-methyl-3,6-pyridazinedione;4-Methyl-1,2,3,6-tetrahydropyridazine-3,6-dione;4-methyl-1,2-dihydropyridazine-3,6-dione
• CAS NO: 5754-18-7
• Molecular Formula: C₅H₆N₂O₂
• Molecular Weight: 126.11
• EINECS: 227-276-7
• Product Categories: Heterocyclic Compounds
• Mol File: 5754-18-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 284-288°C
• Boiling Point: 434.4 °C at 760 mmHg
• Flash Point: 216.5 °C
• Appearance: /
• Density: 1.226 g/cm³
• Vapor Pressure: 3.74E-08mmHg at 25°C
• Refractive Index: 1.489
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.34±0.40(Predicted)
• CAS DataBase Reference: 3,6-Dihydroxy-4-methylpyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Dihydroxy-4-methylpyridazine(5754-18-7)
• EPA Substance Registry System: 3,6-Dihydroxy-4-methylpyridazine(5754-18-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 5754-18-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C5H6N2O2/c1-3-2-4(8)6-7-5(3)9/h2H,1H3,(H,6,8)(H,7,9)

Upstream product

• 14011-37-1 hydrazine dihydrochloride 
• 616-02-4 citraconic acid anhydride 
• 617-54-9 citraconic acid dimethyl ester 
• 117122-49-3 methyl-maleic acid dihydrazide 
• 64-19-7 acetic acid 

Downstream Products

• 73477-02-8 (E)-4-<2-(4-methoxyphenyl)ethenyl>pyridazine 
• 1120-88-3 4-methylpyridazine 
• 89943-29-3 4-Methyl-3,6-dimethoxy-pyridazin 
• 19064-64-3 3,6-dichloro-4-methylpyridazine 
• 34127-22-5 ethyl 3,6-dichloropyridazine-4-carboxylate 
• 717112-50-0 1,2,4-trimethyl-3,6-pyridazinedione 
• 1703-07-7 6-chloro-5-methyl-2H-pyridazin-3-one 
• 1834-27-1 6-chloro-4-methyl-2H-pyridazin-3-one 
• 32193-12-7 methyl-4 (p-chloro phenyl)-6 pyridazone-3 
• 118270-06-7 6-(3-Methoxy-phenyl)-4-methyl-2H-pyridazin-3-one 
• 13300-09-9 4-methyl-6-phenylpyridazin-3(2H)-one 
• 910229-66-2 5-methyl-6-oxo-1,6-dihydropyridazin-3-yl 2,4,6-triisopropylbenzenesulfonate 

Relevant articles and documents

One-step ring condensation of hydrazine derivatives and cyclic anhydrides

Hydroxypyridazinone and pyrroledione rings condensation in the reactions of hydrazine hydrate with citraconic, 2,3-dimethylmaleic, succinic and cis-cyclohexanedicarboxylic anhydrides have been conducted in the HCl aqueous solution. The pyridazine-ring condensation yields products unexpected for these conditions. They have been identified by 1H/13C NMR and X-ray diffraction. The course of the reaction toward the five- and six-membered ring condensation strongly depends on methyl and other substituents in the anhydrides and in hydrazine. The obtained products indicate that the ring condensation is controlled by the molecular strains and steric hindrances between the substituents in anhydrides and pyridazinone products. The condensation of cyclic anhydrides with hydrazines has been reduced to one-step reaction and its yield significantly increased.

Design, synthesis, crystallographic studies, and preliminary biological appraisal of new substituted triazolo[4,3-b]pyridazin-8-amine derivatives as tankyrase inhibitors

Searching for selective tankyrases (TNKSs) inhibitors, a new small series of 6,8-disubstituted triazolo[4,3-b]piridazines has been synthesized and characterized biologically. Structure-based optimization of the starting hit compound NNL (3) prompted us to the discovery of 4-(2-(6-methyl-[1,2,4] triazolo[4,3-b]pyridazin-8-ylamino)ethyl)phenol (12), a low nanomolar selective TNKSs inhibitor working as NAD isostere as ascertained by crystallographic analysis. Preliminary biological data candidate this new class of derivatives as a powerful pharmacological tools in the unraveling of TNKS implications in physiopathological conditions.