34231-77-1

Basic information

• Product Name: Pyridazine-4-carboxylic acid methyl ester
• Synonyms: Pyridazine-4-carboxylic acid methyl ester;Methyl pyridazine-4-carboxylate, 96%;4-Pyridazinecarboxylic acid methyl ester;Methyl 4-pyridazinecarboxylate;4-Methoxycarbonylpyridazine
• CAS NO: 34231-77-1
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12404
• Mol File: 34231-77-1.mol

Chemical Properties

• Melting Point: 64-67℃
• Boiling Point: 281.273 °C at 760 mmHg
• Flash Point: 123.91 °C
• Appearance: /
• Density: 1.214 g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: Pyridazine-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridazine-4-carboxylic acid methyl ester(34231-77-1)
• EPA Substance Registry System: Pyridazine-4-carboxylic acid methyl ester(34231-77-1)

Safety Data

• WGK Germany: nwg
• Hazardous Substances Data: 34231-77-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pyridazine-4-carboxylic acid methyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to form different chemical bonds and react with other molecules makes it a valuable building block for creating new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
In the chemical industry, Pyridazine-4-carboxylic acid methyl ester is used as a starting material for the production of various organic compounds. It can be further modified or reacted with other reagents to create a wide range of products, such as dyes, pigments, and other specialty chemicals.
Used in the Synthesis of 4-Pyridazincarbohydroxamsaeure:
Pyridazine-4-carboxylic acid methyl ester is used as a precursor in the production of 4-Pyridazincarbohydroxamsaeure. This process requires heating the ester with hydroxylammonium chloride and sodium carbonate (Na2CO3) in a solvent like methanol. The resulting compound, 4-Pyridazincarbohydroxamsaeure, has potential applications in various fields, including pharmaceuticals and agrochemicals.

InChI:InChI=1/C6H6N2O2/c1-10-6(9)5-2-3-7-8-4-5/h2-4H,1H3

Upstream product

• 75-52-5 nitromethane 
• 50901-42-3 pyridazine-4-carbaldehyde 
• 67-56-1 methanol 
• 50681-25-9 pyridazine-4-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 124-41-4 sodium methylate 

Downstream Products

• 1434271-66-5 (E)-3-(4-bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-one 
• 1434271-67-6 3-(4-bromophenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one 
• 1434271-68-7 4'-(3-oxo-3-(pyridazin-4-yl)-1-o-tolylpropyl)biphenyl-4-carboxylic acid 
• 1434271-69-8 tert-butyl 4-(4-(3-oxo-3-(pyridazin-4-yl)-1-o-tolylpropyl)phenyl)piperidine-1-carboxylate 
• 103983-86-4 5-phenylpyridazine-4-carboxylic acid 
• 50901-43-4 4-hydroxymethylpyridazine 
• 1434271-70-1 3-(4-(1-(methylsulfonyl)piperidin-4-yl)phenyl)-1-(pyridazin-4-yl)-3-o-tolylpropan-1-one 
• 1232221-96-3 N-(3-methyl-benzylidene)-N'-(7-morpholin-4-yl-2-pyridazin-4-yl-pyrazolo[1,5-a]pyrimidin-5-yl)hydrazine 
• 124436-57-3 2,5-Dihydro-pyridazine-4-carboxylic acid methyl ester 
• 96054-52-3 4-Pyridazincarbohydroxamsaeure 
• 132368-95-7 N-methyl-N-phenyl-4-pyridazinyecarboxamide 
• 132368-97-9 2-(methylamino)phenyl 4-pyridazinyl ketone 
• 132368-99-1 5-chloro-2-(pivaloylamino)phenyl 4-pyridazinyl ketone 
• 132368-98-0 5-chloro-2-(methylamino)phenyl 4-pyridazinyl ketone 

Relevant articles and documents

Triarylamine-based hydrido-carboxylate rhenium(i) complexes as photosensitizers for dye-sensitized solar cells

Two new dyes based on a dinuclear rhenium complex and (E)-3-(5-(4-(bis(2′,4′-dibutoxy-[1,1′-biphenyl]-4-yl)amino)phenyl)thiophen-2-yl)-2-cyanoacrylic acid (namely D35) have been investigated as sensitizers for dye sensitized solar cells (DSSCs). Two different pyridazine ligands have been used, namely 4-pyridazine-carboxylic acid for dye 2 ([Re2(μ-H)(-D35)(CO)6(μ-pyridazine-4-COOH)]) and 4-pyridazinyl-butanoic acid for dye 3 ([Re2(μ-H)(-D35)(CO)6(μ-pyridazine-4-C3H6-COOH)]). The performances of these new dyes have been compared with those of the dye containing the bare 4-diphenylaminobenzoic acid, namely TPA, as the ancillary ligand (dye 1). Compared to dye 1, dyes 2 and 3 show an impressive tenfold increase in the absorption intensity in the range of 487-493 nm on TiO2 films, with great improvement of the light harvesting. Cyclic voltammetry experiments, performed on derivatives containing the methyl ester of the pyridazine ligands, show narrow electrochemical band gaps in the range of 1.36-1.84 eV. Solar cells with each dye have been prepared, using both iodide/triiodide and cobalt redox couples as the electrolytes, platinum or carbon as the counter electrodes, and TiO2 or SnO2 as the metal oxide photoelectrodes, respectively. The best DSSC results have been obtained using dye 3, with an overall solar-to-electric conversion efficiency of 3.5%, which greatly overcomes the previous result of 1.0% obtained for dye 1 in a not-optimized setup of the device. The performances of dye 3 are due to the presence of D35 ligand, which further suppresses the recombination of the injected electron with the electrolyte and with the oxidized state of the dye.

HERBICIDAL COMPOUNDS

Use of the compounds of the formula (I) wherein the substituents are as defined herein as herbicides. Compounds of formula (I) are also claimed.

An anthrone-based Kv7.2/7.3 channel blocker with improved properties for the investigation of psychiatric and neurodegenerative disorders

A set of novel Kv7.2/7.3 (KCNQ2/3) channel blockers was synthesized to address several liabilities of the known compounds XE991 (metabolic instability and CYP inhibition) and the clinical compound DMP 543 (acid instability, insolubility, and lipophilicity). Using the anthrone scaffold of the prior channel blockers, alternative heteroarylmethyl substituents were installed via enolate alkylation reactions. Incorporation of a pyridazine and a fluorinated pyridine gave an analog (compound 18, JDP-107) with a promising combination of potency (IC50 = 0.16 μM in a Kv7.2 thallium flux assay), efficacy in a Kv7.2/7.3 patch clamp assay, and drug-like properties.

New dinuclear hydrido-carbonyl rhenium complexes designed as photosensitizers in dye-sensitized solar cells

The possible use of some dinuclear rhenium complexes as sensitizers for dye sensitized solar cells (DSSCs) has been investigated. They have general formula [Re2(μ-X)(μ-Y)(CO)6(μ-pyridazine-4-COOH)], with X = Y = Cl (1), X = H, Y = benzoato (2), and X = H, Y = 4-diphenylaminobenzoato (3). An original synthetic strategy has been set for preparing the hydrido-carboxylato derivatives 2 and 3. They have been indicated by DFT and TD-DFT computations as the most promising dyes, endowed with good light harvesting capability. The complexes have absorption maxima in the range of 405-443 nm, on TiO2 films, arising from metal-to-ligand-charge transfer transitions. Cyclic voltammetry experiments have been performed on the derivatives containing the methyl ester of the pyridazine-4-COOH acid, showing electrochemical band gaps in the range of 2.25-1.63 eV. The best DSSC results have been obtained using complex 3, with an overall solar-to-electric conversion efficiency of 1.0%. Noteworthy the presence of a hydrido ligand did not show any detrimental effect on the stability of the sensitizers under the operating conditions.

NOVEL 1,2,4 OXADIAZOLE COMPOUNDS AND METHODS OF USE THEREOF

The invention relates to 1,2,4 oxadiazole compounds and analogs thereof, represented by formula (II), and compositions and methods of use thereof.

3- (1,2,4-TRIAZOL-3YLALKYL) AZABRICLO (3.1.0) HEXANE DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS

The present invention relates to novel compounds of formula (I) or pharmaceutically acceptable salt thereof: wherein " G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl and indazolyl; " p is an integer ranging from 0 to 5; " R1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and SF5, or corresponds to a group R5; " each R2 is independently hydrogen, fluorine or C1-4alkyl; " n is 2, 3, 4, or 5; " R3 is C1-4alkyl; " R4 is hydrogen, or a C1-4alkyl group, a benzyl group, a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl and SF5;or R4 is a -SR6 group; " R5 is selected from a group consisting of: isoxazolyl, -CH2-N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl and 2-pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from a group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy and C1-4alkanoyl; " R6 is C1-4alkyl or -CH2C3-4cycloalkyl; and when R1 is chlorine and p is 1, such R1 is not present in the ortho position with respect to the linking bond to the rest of the molecule; and when R1 corresponds to R5, p is 1. processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D3 receptors, e.g. to treat drug dependency, as antipsychotic agents, to treat obsessive compulsive spectrum disorders, premature ejaculation or cognition impairment.

Pyridazines.LI. On the Reactivity of Pyridazinecarbaldehydes towards Selected Active-Hydrogen Compounds

Reactions of 3-pyridazinecarbaldehyde and 3-pyridazinecarbaldehyde with various active methylene carbanions were studied.The products obtained in Knoevenagel reactions, Wittig-Horner-Emmons reactions, and Hantzsch-type reactions are presented.

Synthesis and antiviral activity of thiosemicarbazone derivatives of pyridazinecarbaldehydes and alkyl pyridazinyl ketones

Various novel thiosemicarbazones (TSCs) 15b-e, 16b-e, 17b-e, 18b-e, and 19b-e derived from 4-pyridazinecarbaldehyde, 3-pyridazinecarbaldehyde, 4-acetylpyridazine, 3-acetylpyridazine, and 3-propionylpyridazine were prepared and their cytotoxic and antiherpetic potentials were evaluated. It was found that the replacement of the 2-pyridyl-moiety in aldehyde derived compounds 20a-c by a 4-pyridazinyl group (compounds 15b-d) abolishes biological activity. However, in TSCs derived from 3-pyridazinecarbaldehyde (16b-d) the cytotoxic potency was considerably reduced (factor ~300), while the antiviral activity was largely retained. A total loss of biological activity occurred when the pyridyl group in TSC 20d, derived from 2-acetylpyridine, was replaced by the 4-pyridazinyl system (17d). By employment of the 3-pyridazinyl unit for isosteric modification, however, the cell toxicity could be reduced significantly (factor 100) without impairing the antiherpetic potential also in the series of TSCs derived from N-heteroaromatic ketones. It was observed that there is no obvious influence of the size of the cycloamino substituent on the biological activities in compounds 20a-d, 15b-d, 16b-d, 17b-d, and 18b-d. While the pyridine derived TSCs in our experiments proved clearly cytotoxic at lower concentrations than those being antivirally active, the aza-analogous compounds derived from 3-acetyl-pyridazine (18b-e) inhibited plaque formation at concentrations equal to those causing cytotoxic effects. The TSCs 16b-e derived from 3-pyridazinecarbaldehyde were found to show selective antiviral activity against HSV-1. In addition, a significant improvement of the water solubility of heteroaromatic TSCs could be achieved by the replacement of the CH-moiety in position 6 of the pyridine derivatives 20a-c by a nitrogen atom (compounds 16b-d).