92184-43-5

Basic information

• Product Name: 4-PHENYLPYRIDAZINE
• Synonyms: 4-PHENYLPYRIDAZINE;Pyridazine, 4-phenyl-
• CAS NO: 92184-43-5
• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.18
• EINECS: 938-254-8
• Mol File: 92184-43-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 86-86.5 °C
• Boiling Point: 349.6±21.0 °C(Predicted)
• Appearance: /
• Density: 1.106±0.06 g/cm3(Predicted)
• PKA: 2.77±0.10(Predicted)
• CAS DataBase Reference: 4-PHENYLPYRIDAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYLPYRIDAZINE(92184-43-5)
• EPA Substance Registry System: 4-PHENYLPYRIDAZINE(92184-43-5)

Safety Data

• Hazardous Substances Data: 92184-43-5(Hazardous Substances Data)

Usage

General Description

4-Phenylpyridazine is a chemical compound with the molecular formula C10H8N2. It is a heterocyclic aromatic compound that consists of a pyridine ring with a phenyl group attached at the 4-position. 4-Phenylpyridazine is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has also been investigated for its potential biological activities, including its antiproliferative and anticancer properties. Additionally, 4-phenylpyridazine has been studied for its potential as a photosensitizer in photodynamic therapy for cancer treatment. Overall, 4-phenylpyridazine is a versatile compound with potential applications in the fields of medicine, agriculture, and materials science.

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Relevant articles and documents

Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding

An unprecedented 1,4-cycloaddition (vs 3,6-cycloaddition) of 1,2,4,5-tetrazines is described with preformed or in situ generated aryl-conjugated enamines promoted by the solvent hydrogen bonding of hexafluoroisopropanol (HFIP) that is conducted under mild reaction conditions (0.1 M HFIP, 25 °C, 12 h). The reaction constitutes a formal [4 + 2] cycloaddition across the two nitrogen atoms (N1/N4) of the 1,2,4,5-tetrazine followed by a formal retro [4 + 2] cycloaddition loss of a nitrile and aromatization to generate a 1,2,4-triazine derivative. The factors that impact the remarkable change in the reaction mode, optimization of reaction parameters, the scope and simplification of its implementation through in situ enamine generation from aldehydes and ketones, the reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, a survey of participating 1,2,4,5-tetrazines, and key mechanistic insights into this reaction are detailed. Given its simplicity and breath, the study establishes a novel method for the simple and efficient one-step synthesis of 1,2,4-triazines under mild conditions from readily accessible starting materials. Whereas alternative protic solvents (e.g., MeOH vs HFIP) provide products of the conventional 3,6-cycoladdition, the enhanced hydrogen bonding capability of HFIP uniquely results in promotion of the unprecedented formal 1,4-cycloaddition. As such, the studies represent an example of not just an enhancement in the rate or efficiency of a heterocyclic azadiene cycloaddition by hydrogen bonding catalysis but also the first to alter the mode (N1/N4 vs C3/C6) of cycloaddition.

COPPER-CATALYZED C-H BOND ARYLATION

The present invention is a one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using a combination of aryl halides, a substrate, and a copper salt as catalyst. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores and explosives.

A general method for copper-catalyzed arylation of arene C-H bonds

A general method for copper-catalyzed arylation of sp2 C-H bonds with pKa's below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K3PO4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper-phenanthroline complex intermediates were independently synthesized.