1126-00-7

Usage

Uses

1-Phenylpyrazole is used as a key component in the synthesis of various complex organic molecules, such as 4,5-diphenylpyrazolo[1,5-a]quinoline, 1-(1,2,3,4-tetraphenylnaphthalen-5-yl)pyrazole, and 1-(1,2,3,4,5,6,7,8-octaphenylanthracen-9-yl)pyrazole. These compounds have potential applications in various fields, including pharmaceuticals and materials science.
Used in Chemical Synthesis:
1-Phenylpyrazole is used as a cyclometallated ligand for the preparation of new heteroleptic iridium(III) complexes. These complexes are of interest in the field of organometallic chemistry and have potential applications in areas such as catalysis and photovoltaics.

InChI:InChI=1/C9H8N2/c1-2-5-9(6-3-1)11-8-4-7-10-11/h1-8H

Upstream product

• 52066-48-5 1-phenyl-pyrazolidin-4-ol 
• 59-88-1 phenylhydrazine hydrochloride 
• 71-43-2 benzene 
• 1134-50-5 4-carboxy-1-phenylpyrazole 
• 16078-70-9 2-phenyl-2H-pyrazole-3,4-dicarboxylic acid 
• 616-23-9 2,3-Dichloro-1-propanol 
• 100-63-0 phenylhydrazine 
• 96-11-7 1,2,3-tribromopropane 
• 106-89-8 epichlorohydrin 
• 1216-15-5 cinnamaldehyde phenylhydrazone 
• 288-13-1 NH-pyrazole 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 7647-01-0 hydrogenchloride 
• 10160-87-9 Propiolaldehyde diethyl acetal 

Downstream Products

• 35267-14-2 N-phenylpyrazolidine 
• 6831-92-1 4-Chloro-1-phenyl-1H-pyrazole 
• 4742-01-2 N-(3-aminopropyl)aniline 
• 613686-09-2 1-(2-(1H-pyrazol-1-yl)phenyl)propan-1-one 
• 173457-38-0 5-((S)-2-(3,4-dichlorophenyl)-4-pentenoyl)-1-phenylpyrazole 
• 173654-00-7 5-[(1R,2S)-2-(3,4-dichlorophenyl)-1-hydroxy-4-pentenyl]-1-phenyl-1,2,3-(1H)-triazole 
• 35715-71-0 1-phenyl-4-pyrazolylmethyl chloride 
• 562824-23-1 tris(1-phenyl-κC1-pyrazolato-κN2)iridium 
• 1078735-77-9 C₁₇H₁₂N₂S₂ 
• 6831-89-6 1,5-diphenyl-1H-pyrazole 
• 1193686-44-0 1-phenyl-5-(phenylthio)-1H-pyrazole 
• 25775-03-5 2-(1H-pyrazol-1-yl)-benzonitrile 
• 1254162-97-4 2-((2,6-di-2-thienyl)phenyl)pyrazole 
• 1254163-01-3 6,6'-(2-(1H-pyrazolyl)-1,3-phenylene)bis(2-methylpyridine) 

Relevant academic research and scientific papers

Highly practical "ligand-free-like" copper-catalyzed N-arylation of azoles in lower nitrile solvents

In lower nitrile solvents, the N-arylation of azoles with aryl halides was achieved efficiently in the presence of copper powder without any additional ligands. Thus, the first nitrile type of monodentate ligand-mediated, "ligand-free-like" copper-catalyzed N-arylation procedure was established.

α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles

The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C-N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-Arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.

CuI heterogenized on thiosemicarbazide modified-multi walled carbon nanotubes (thiosemicarbazide-MWCNTs-CuI): Novel heterogeneous and reusable nanocatalyst in the C-N Ullmann coupling reactions

Herein we described the synthesis of novel thiosemicarbazide-MWCNTs-CuI nanocatalyst by covalent grafting of thiosemicarbazide on carbon nanotubes surface and subsequent coordination with CuI catalyst. The formation of nanocatalyst was analyzed by Raman spectroscopy, energy dispersive spectroscopy (EDS), wavelength-dispersive X-ray spectroscopy (WDX) and ICP analysis. The morphology of the nanocatalyst was characterized using scanning and transmission electron microscopes (SEM and TEM). Additionally, the (thiosemicarbazide-MWCNTs-CuI) nanocatalyst was successfully employed in the N-arylation of indole, amines and imidazoles through intermolecular C(aryl)-N bond formation from the corresponding aryl halides (Ar–I, Ar–Br, Ar–Cl) with amines through Ullmann-type coupling reactions. Interestingly, the novel catalyst could be recovered and recycled five times.

Efficient iron-catalyzed N-arylation of aryl halides with amines

(Chemical Equation Presented) A practical and promising protocol was developed for N-arylations of various amines with differently substituted aryl halides. The processes are efficiently promoted by the catalyst system involving the environmentally benign Fe2O3 and the universal ligand L-proline. The versatility, convenient operation, low cost, and environmental friendliness, in combination with the high yields, render this method viable for use in both laboratory research and larger industrial scales.

A ligand-free copper-catalyzed strategy to the N-arylation of indazole using aryl bromides

A simple and efficient strategy for the C–N cross-coupling of indazole with a variety of substituted aryl bromides is reported. Under the optimized conditions, a broad scope of N-arylated products were obtained in good to excellent yields (up to 87%) under the ligand-free conditions.

Cooperatively assisted N-arylation using organic ionic base-Br?nsted acid combination under controlled microwave heating

A new synthetic strategy is developed for the construction of C-N bond through the assistance of Br?nsted acid/[DBU][HOAc] without adding any metal catalyst. This is the first efficient SNAr methodology utilizing fluoro, chloro, bromo, and iodoarenes as coupling partners, which offers excellent yield up to 94% within a very short time.

Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles

(Chemical Equation Presented) An ideal pair: Various substituted aryl halides react under mild conditions with nitrogen heterocycles in the presence of catalytic amounts of [Fe(acac)3] (acac = acetylacetonate) and copper salts to give the corresponding cross-coupling products in high yields (see scheme). This cheap and environmentally friendly cocatalyst system is the first example of cooperative Fe/Cu catalysis in this type of N-C bond formation.

Facile Synthesis of 1-Arylpyrazoles

A convenient and transition-metal-free synthesis of 1-arylpyrazoles that involves the cycloaddition of 3-arylsydnones and acrylic acid is presented. The process proceeds smoothly to obtain the target products with moderate to high yields.

Cooperative Au/Ag Dual-Catalyzed Cross-Dehydrogenative Biaryl Coupling: Reaction Development and Mechanistic Insight

An operationally simple and highly selective Au/Ag bimetallic-catalyzed cross-dehydrogenative biaryl coupling between pyrazoles and fluoroarenes has been developed. With this reaction, a wide range of biheteroaryl products can be obtained in moderate to good yields with excellent functional group compatibility. The exact role of silver salts, previously overlooked in most gold-catalyzed transformations, has been carefully investigated in this biaryl coupling. Insightful experimental and theoretical studies indicate that silver acetate is the actual catalyst for C-H activation of electron-poor arenes, rather than the previously reported gold(I)-catalyzed process. An unprecedented Au/Ag dual catalysis is proposed, in which silver(I) is responsible for the activation of electron-poor fluoroarenes via a concerted metalation-deprotonation pathway, and gold(III) is responsible for the activation of electron-rich pyrazoles via an electrophilic aromatic substitution process. Kinetic studies reveal that ArFnAu(III)-mediated C-H activation of pyrazoles is most likely the rate-limiting step.

Copper ferrite nanoparticle-mediated N-arylation of heterocycles: A ligand-free reaction

The synergistic effects of iron and copper in copper ferrite nanoparticles for the N-arylation of heterocycles with aryl halides were demonstrated. The magnetic nature of the catalyst facilitates its removal from the reaction medium for further use. Negligible leaching of Cu and Fe in consecutive cycles makes the catalyst economical and environmentally benign for C-N cross-coupling reactions.