289-80-5

Basic information

• Product Name: Pyridazine
• Synonyms: 1,2-Diazabenzene;o-diazine;Pyridazin;1,2-DIAZINE;AKOS 92457;ORTHODIAZINE;OIZINE;PYRIDAZINE
• CAS NO: 289-80-5
• Molecular Formula: C₄H₄N₂
• Molecular Weight: 80.09
• EINECS: 206-025-5
• Product Categories: Heterocycles;Organoborons;Pyridazine;Building Blocks;Heterocyclic Building Blocks;Pyridazines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 289-80-5.mol
• Article Data: 29

Chemical Properties

• Melting Point: −8 °C(lit.)
• Boiling Point: 208 °C(lit.)
• Flash Point: 185 °F
• Appearance: Clear yellow-brown/Liquid
• Density: 1.103 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.315mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Storage Temp.: Refrigerator
• PKA: 2.24(at 20℃)
• Water Solubility: MISCIBLE
• Merck: 14,7969
• BRN: 103906
• CAS DataBase Reference: Pyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridazine(289-80-5)
• EPA Substance Registry System: Pyridazine(289-80-5)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 23-24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• RTECS: UR5267000
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 289-80-5(Hazardous Substances Data)

Usage

Chemical Description

Pyridazine is a heterocyclic compound containing a six-membered ring with two nitrogen atoms.

Uses

Used in Pharmaceutical Industry:
Pyridazine is used as a key component in the development of various pharmaceutical drugs for its ability to improve the physiochemical properties of drug molecules, increase water solubility, and enhance bioavailability, particularly to the CNS. It is a part of several drug molecules, such as cefozopran, olaparib, talazoparib, and cadralazine.
Used in Herbicide Industry:
Pyridazine is used as an active ingredient in the formulation of herbicides like credazine and pyridatol, where its chemical properties contribute to the effectiveness of these products in controlling weed growth.
Used in Chemical Synthesis:
Pyridazine is used as a starting material or intermediate in the synthesis of various N-bridgehead aromatic heterocycles, such as pyrrolo[1,2-b]pyridazine 1, which is obtained by the condensation of pyridazine and pyrrole. This application showcases the versatility of pyridazine in chemical reactions and its potential for creating complex molecular structures.
Chemical Properties:
Pyridazine is a clear yellowish-brown liquid, which indicates its physical state and color for identification and handling purposes.

Heterocyclic compound

Pyridazine refers to a heterocyclic azine compound containing a nitrogen hexaheterocyclic , it and pyrimidine, pyrazine are isomers of each other , it is insoluble in petroleum ether, soluble in methanol, ethanol and ether, and it can be miscible with water, benzene and dimethyl formamide immiscibility. Pyridazine is a weak base, which can form salts with picric acid, and hydrochloric acid; pyridazine is not prone to nucleophilic and electrophilic aromatic substitution reaction; it is stable to potassium permanganate; sodium or alcohols may be reduced open-chain , and converted to 1,4-diaminobutane. Pyridazine is widely used as pharmaceutical raw materials, such as long-term sulfa SMP which is pyridazine derivative, 4-amino-cinnoline which belongs to antimalarials, blood pressure drug hydralazine, etc. all use pyridazine as raw materials; it can also be used as raw material of pesticides, for the production of herbicides, "herbicide-sensitive", "Milstem", "bromine herbicide-sensitive", "Kusakira," "maleic hydrazide", "Norflurazon", "pyridate "" insecticide "," imputed phosphorus "and so on.

Synthesis and Structure

Pyridazines are heterocyclic compounds with an N-N bond in their ring structure. The pyridazine molecule is a π-deficient heteroaromatic compound similar to pyridine. Due to the presence of the π-deficient nitrogen aromatic heterocycles these compounds are more easily soluble in water when compared to other hydrocarbons. The basic aromatic ring system of pyridazine contains two adjacent nitrogen atoms. The parent heterocycle was first prepared by oxidation of benzocinnoline to the pyridazinetetracarboxylic acid followed by decarboxylation. A better route to this otherwise esoteric compound starts with the maleic hydrazide. These heterocycles are often prepared via condensation of 1,4-diketones or 4-ketoacids with hydrazines. Pyridazines are effective water oxidation catalysts with high efficiency turnover numbers up to 700.

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C4H4N2/c1-2-4-6-5-3-1/h1-4H

Upstream product

• 110-00-9 furan 
• 108-24-7 acetic anhydride 
• 141-30-0 3,6-dichlorpyridazine 
• 2164-61-6 pyridazine-3-carboxylic acid 
• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 
• 7093-88-1 2,5-dihydro-2,5-diacetoxyfuran 
• 28104-26-9 5-nitro-2,5-dihydrofuran-2-yl acetate 
• 626-60-8 3-Chloropyridine 
• 1457-42-7 pyridazinyl-N-oxide 
• 114068-57-4 3,4-Diaza-tricyclo[3.1.0.0^2,6]hex-3-ene 
• 90230-87-8 3-Benzylpyridazine 2-oxide 
• 108-88-3 toluene 
• 1120-95-2 3-chloropyridazine 
• 10034-85-2 hydrogen iodide 

Downstream Products

• 92184-43-5 4-phenylpyridazine 
• 27666-85-9 4,5-diphenylpyridazine 
• 15150-84-2 3-phenylpyridazine 
• 1457-42-7 pyridazinyl-N-oxide 
• 110-60-1 1,4-diaminobutane 
• 39123-39-2 ethyl pyridazine-4-carboxylate 
• 98832-77-0 triethyl 3,4,5-pyridazinetricarboxylate 
• 98832-78-1 tetraethyl 3,4,5-pyridazinetetracarboxylate 
• 21050-73-7 diethyl pyridazine-4,5-dicarboxylate 
• 1120-88-3 4-methylpyridazine 
• 1632-76-4 3-methylpyridazine 
• 68206-10-0 3,4-dimethylpyridazine 
• 38283-35-1 4,5-dimethylpyridazine 
• 22863-58-7 3,5-dimethyl-pyridazine 

Relevant articles and documents

Approaches to open fullerenes: Synthesis and kinetic stability of Diels-Alder adducts of substituted isobenzofurans and C60

(Chemical Equation Presented) We have examined the reactions of 1,3-disubstituted isobenzofurans with the fullerene C60 in the context of an approach to open a large orifice on the fullerene framework. A variety of substituted isobenzofurans (6a-h), generated from the reaction of 1,4-substituted 1,4-epoxynaphthalenes 3a-h with 3,6-bis(2-pyridyl)-1,2,4,5- tetrazine (4a) or 1,2,4,5-tetrazine (4b), were added to C60 to afford the Diels-Alder adducts 7a-h. The thermal stability of these adducts toward retro-Diels-Alder fragmentation differs greatly in solution from that in the solid state. In solution, the relatively facile retro-Diels-Alder fragmentation of monoadducts 7a and 7c, to give C60 and the free isobenzofurans 6a and 6c, have rate constants (and activation barriers) of k = 9.29 × 10-5 s-1 at 70°C (Ea = 32.6 kcal mol -1) and k = 1.36 × 10-4 s-1 at 40°C (Ea = 33.7 kcal mol-1), respectively, indicating that the addition of isobenzofurans to C60 is readily reversible at those temperatures. In the solid state, thermogravimetric analysis of adduct 7a indicates that its decomposition occurs only within the temperature range of 220-300°C. As a result, these compounds can be stored at room temperature in the solid state for several weeks without significant decomposition but have to be handled within several hours in solution.

One-Pot and Two-Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D-Labeled Derivatives

Acetylene surrogates are efficient tools in modern organic chemistry with largely unexplored potential in the construction of heterocyclic cores. Two novel synthetic paths to 3,6-disubstituted pyridazines were proposed using readily available acetylene surrogates through flexible C2 unit installation procedures in a common reaction space mode (one-pot) and distributed reaction space mode (two-chamber): (1) an interaction of 1,2,4,5-tetrazine and its acceptor-functionalized derivatives with a CaC2?H2O mixture performed in a two-chamber reactor led to the corresponding pyridazines in quantitative yields; (2) [4+2] cycloaddition of 1,2,4,5-tetrazines to benzyl vinyl ether can be considered a universal synthetic path to a wide range of pyridazines. Replacing water with D2O and vinyl ether with its trideuterated analog in the developed procedures, a range of 4,5-dideuteropyridazines of 95–99% deuteration degree was synthesized for the first time. Quantum chemical modeling allowed to quantify the substituent effect in both synthetic pathways.

Synthesis of novel 7-azaindole derivatives containing pyridin-3-ylmethyl dithiocarbamate moiety as potent PKM2 activators and PKM2 nucleus translocation inhibitors

Multiple lines of evidence have indicated that pyruvate kinase M2 (PKM2) is upregulated in most cancer cells and it is increasingly recognized as a potential therapeutic target in oncology. In a continuation of our discovery of lead compound 5 and SAR study, the 7-azaindole moiety in compound 5 was systematically optimized. The results showed that compound 6f, which has a difluoroethyl substitution on the 7-azaindole ring, exhibited high PKM2 activation potency and anti-proliferation activities on A375 cell lines. In a xenograft mouse model, oral administration of compound 6f led to significant tumor regression without obvious toxicity. Further mechanistic studies revealed that 6f could influence the translocation of PKM2 into nucleus, as well as induction of apoptosis and autophagy of A375 cells. More importantly, compound 6f significantly inhibited migration of A375 cells in a concentration-dependent manner. Collectively, 6f may serve as a lead compound in the development of potent PKM2 activators for cancer therapy.

Efficient synthesis of pyrazine boronic esters via palladium-catalyzed Miyaura borylation

A facile and efficient protocol for palladium-catalyzed Miyaura borylation reaction of chloropyrazines with B2pin2has been developed. A certain range of difficult-to-access pyrazine boronic esters can be easily prepared from the corresponding chloropyrazines in moderate to good yields.

METHODS OF INCORPORATING AN AMINO ACID COMPRISING A BCN GROUP INTO A POLYPEPTIDE USING AN ORTHOGONAL CODON ENCODING IT AND AN ORTHORGONAL PYLRS SYNTHASE

The invention relates to a polypeptide comprising an amino acid having a bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN) group, particularly when said BCN group is present as: a residue of a lysine amino acid. The invention also relates to a method of producing a polypeptide comprising a BCN group, said method comprising genetically incorporating an amino acid comprising a BCN group into a polypeptide. The invention also relates to an amino acid comprising bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN), particularly and amino acid which is bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN) lysine. In addition the invention relates to a PylRS tRNA synthetase comprising the mutations Y271M, L274G and C313A.

ALPHA-HELIX MIMETIC WITH FUNCTIONALIZED PYRIDAZINE

The synthesis of new α-helix scaffolds mimicking i, i+3 or i+4, i+7 residues, was accomplished. The common pyridazine heterocycle originates from the easily available dimethyl pyridazine-3,6-dicarboxylate building block. These scaffolds may be thought of as synthetic counterparts of amphiphilic α-helices having a hydrophilic face along one side and a hydrophobic face along the other side of the helix.

Experimental and theoretical characterization of the valence isomerization of Bi-2H-azirin-2-yls to diazabenzenes

3,4-Diazidocyclobutenes 16 were prepared from the corresponding dihalides. Some of these diazides, such as parent compound 16 d and phenyl-substituted derivatives 16c,f, underwent spontaneous stereoselective electrocyclic ring opening below room temperature, whereas the tetraalkyl derivatives of 16 had to be heated to force the same reaction. In most cases, the resulting 1,4-diazidobuta-1,3-dienes 8 were isolated to study their photochemical transformation into bi-2Hazirin-2-yls 9 via intermediate monoazirines 17. Except for starting materials with a low number of substituents such as 9d and 9f, title compounds 9 underwent a thermal valence isomerization which led exclusively to pyridazines 18 at surprisingly low temperatures. Based on quantum-chemical calculations for the parent bi-2H-azirinyl 2-yl 9d at the UB3LYP/6-31+G(d) and MR-MP2/TZV(2df,2p) levels, the valence isomerization process is best explained by simultaneous homolytic cleavage of both C-N single bonds of 9 to generate energetically favorable N,N′ diradicals 26, which cyclize to 18. The theoretical studies indicate also that one stereoisomer of 9, namely, the rac compound, should undergo valence isomerization more easily than the other, which is in conformity with different rates of these rearrangement reactions found experimentally. For the tetramethyl-bi-2H-azirin-2-yls 9g, which are better models for the experimentally studied compounds, simultaneous homolytic cleavage of both C-N single bonds is also predicted by the calculations, although the intermediate diradicals 26 g are significantly higher in energy than those of the parent system 9d.

Inhibitors of protein kinase for the treatment of disease

The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.

Trisubstituted heterocyclic compounds and their use as fungicides

Compounds of general formula (I): in which:Het represents a five or six membered saturated, partially unsaturated or aromatic ring containing between one and six heteroatoms of the group N, O, S, in which the heterocycle is substituted in an adjacent manner with -P-Q1-T-Q2, -GZ and Y, such that the substituant -GZ is adjacent to both. the other substituants being as defined in the description,process for preparing these compounds,fungicidal compositions comprising these compounds,processes for treating plants by applying these compounds or compositions.

Novel compounds

The present invention is directed to novel pyridazine compounds of the formula I as well as pharmaceutically and pharmacologically acceptable salts, and hydrates thereof; to a process for their preparation, their use and pharmaceutical compositions comprising said novel compounds. These novel compounds are useful in therapy, particularly for the treatment of type 2 diabetes mellitus.