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

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

Uses

Used in Pharmaceutical Industry:
4-Phenylpyridazine is used as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Phenylpyridazine serves as an intermediate in the production of agrochemicals, which are essential for enhancing crop protection and yield.
Used in Cancer Research:
4-Phenylpyridazine has been investigated for its potential biological activities, particularly its antiproliferative and anticancer properties. It holds promise as a candidate for further research and development in oncology.
Used in Photodynamic Therapy:
Additionally, 4-Phenylpyridazine has been studied for its potential as a photosensitizer in photodynamic therapy for cancer treatment, offering a novel approach to combat cancer cells with light-activated chemical reactions.

Upstream product

• 289-80-5 1,2-diazine 
• 938-81-8 N-nitrosoacetanilide 
• 100-34-5 benzene diazonium chloride 
• 36966-84-4 benzenediazohydroxide 
• 94-36-0 dibenzoyl peroxide 
• 103983-86-4 5-phenylpyridazine-4-carboxylic acid 
• 863422-41-7 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridazine 
• 591-50-4 iodobenzene 
• 290-96-0 s-Tetrazine 
• 122-78-1 phenylacetaldehyde 
• 41373-90-4 4-Phenyl-3,6-dioxo-1,2,3,6-tetrahydropyridazine 
• 2166-27-0 4-phenyl-pyridazine-3,6-dicarboxylic acid dimethyl ester 
• 91330-47-1 5-phenyl-pyridazine-3,4-dicarboxylic acid 
• 194865-89-9 4-(tributylstannanyl)pyridazine 

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.

Selective aryl radical transfers into N-heteroaromatics from diaryliodonoium salts with trimethoxybenzene auxiliary

We have found that a series of trimethoxybenzene-based diaryliodonium(III) salts I (ArI+Ar’X-, where Ar = various aryl groups, Ar’ = 2,4,6-trimethoxyphenyl, X- = counterion) can exclusively cause Ar-transfers during the base-induced radical couplings with N-heteroaromatic compounds 1 by working the trimethoxybenzene ring (Ar’) as an inert coupling auxiliary. By the treatment with N-heteroaromatics 1 as the solvent, the metal-free arylations utilizing the specific salts I initiated by solid NaOH upon heating selectively produced the corresponding biaryls 2 in good yields without the formation of the trimethoxybenzene (Ar’) coupling product.

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.

Deprotonative zincation of heteroaromatics using ZnI2 and tert-Bu-P4 base

The direct deprotonative zincation of diazines was accomplished using the combination of ZnI2 and t-Bu-P4 base and unique regioselectivities of zincation were observed.

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.

Potassium t-butoxide alone can promote the biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes

(Chemical Equation Presented) The biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes can be promoted by potassium t-butoxide alone, without the addition of any exogenous transition metal species. Electron-deficient nitrogen heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, and quinoxaline are arylated with haloarenes. Control experiments support a radical-based mechanism. Taking these findings into account, radical processes may be partially involved in the reported transition-metal-catalyzed arylation reactions employing t-butoxide bases and haloarenes under elevated temperatures or under microwave irradiation.

Synthesis of highly substituted pyridazines through alkynyl boronic ester cycloaddition reactions

(Chemical Equation Presented) A highly regioselective transformation of tetrazines through a cycloaddition reaction with alkynyl boronic esters provides highly substituted pyridazine boronic esters as intermediates for C-O and C-C bond-forming reactions (see scheme). Functionalization reactions of the C-B bond, such as oxidation and the Suzuki cross-coupling, show the versatility of these species.

MR3-substituted alkynes 2 and 3 (M = Si, Ge, Sn; R = alkyl) show high reactivity in inverse-type Diels-Alder reactions with the re-electron-deficient 1,2,4,5-tetrazine 1 in strict contrast to the corresponding carbon compounds.

MR3-substituted alkynes 2 and 3 (M = Si, Ge, Sn; R = alkyl) show high reactivity in inverse-type Diels-Alder reactions with the re-electron-deficient 1,2,4,5-tetrazine 1 in strict contrast to the corresponding carbon compounds. Kinetic data prove the huge accelerating effect of the trialkyltin substituent, offering a simple access to new heteroaromatic organotin derivatives, which can be easily transformed by standard methods of organotin chemistry.

Ab initio quantum-mechanical and experimental mechanistic studies of Diels-Alder reactions between unsubstituted and phenyl-substituted acetylenes and 1,2,4,5-tetrazines

1,2,4,5-tetrazine (2a) undergoes thermal addition to phenylacetylene (1b) in dioxane with ΔH? = 15.8 kcal/mol and ΔS? = -31 cal/(mol·K). The activation parameters for the corresponding addition of 1b to 3-phenyl-1,2,4,5-tetrazine (2b

QUANTITATIVE DETERMINATION OF THE ELECTRONIC EFFECTS OF 3- AND 4-PYRIDAZINYL GROUPS FROM NMR SPECTRAL DATA FOR ISOMERIC AMINOPHENYL- AND PHENYLPYRIDAZINES

The previously unknown aminophenylpyridazines were synthesized.The inductive and resonance constants of 3- and 4-pyridazinyl groups were calculated on the basis of 1H and 13C NMR spectral data for isomeric aminophenyl- and phenylpyridazines in dimethyl sulfoxide (DMSO).