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.

Description

Pyridazine, also known as 1,2-diazine, is a six-membered ring containing two adjacent nitrogen atoms. It is a mono-basic 1,2-diazine compound, commonly prepared by the reaction of 1,4-dicarbonyls with hydrazines. Pyridazine is a privileged structure in medicinal chemistry and can be used as an isosteric replacement of phenyl or heteroaromatic rings. It is found in many herbicides and pharmaceutical drugs, and its structure can improve the physiochemical properties of drug molecules by increasing their water solubility, participating as hydrogen bond acceptors, and having a high capacity to complex with targets due to their dipole moment. Pyridazine confers bioavailability, especially to the CNS, and can reduce toxicity.

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 
• 1120-95-2 3-chloropyridazine 
• 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 
• 6922-38-9 1,1,4,4-tetramethoxy-but-2c-ene 
• 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 
• 90510-96-6 4,4-Diethoxy-3-hydroxy-butyraldehyde 

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

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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.

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.

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.