63532-66-1

Usage

Pyrazole derivative

A five-membered heterocyclic ring containing two nitrogen atoms This describes the core structure of the compound, which is based on a pyrazole ring.

Aromatic nitro compound

Presence of a nitro group and a phenyl group The compound contains a nitro group (-NO2) and a phenyl group (a ring of six carbon atoms with a hydrogen atom), which gives it the properties of an aromatic nitro compound.

Used in organic synthesis and medicinal chemistry

Development of various pharmaceutical drugs and biologically active compounds The compound is commonly used in the synthesis of new drugs and other biologically active molecules.

Potential applications

Agrochemicals, pharmaceuticals, and materials science The compound has potential uses in a variety of fields, including agriculture, medicine, and materials science.

Valuable and versatile building block

Synthesis of new compounds with varied biological and chemical activities The chemical structure and properties of 1H-Pyrazole, 3-(4-nitrophenyl)-5-phenylmake it a useful starting point for creating new compounds with diverse applications.

Upstream product

• 5400-95-3 1-(4-nitro-phenyl)-3-phenyl-propane-1,3-dione 
• 20432-02-4 (E)-4'-nitrochalcone 
• 64-19-7 acetic acid 
• 555-16-8 4-nitrobenzaldehdye 
• 13466-30-3 (1-phenylethylidene)hydrazine 
• 98-86-2 acetophenone 
• 1747-50-8 4-methyl-N'-[(4-nitrophenyl)methylidene]benzene-1-sulfonohydrazide 
• 536-74-3 phenylacetylene 
• 100-19-6 (4-nitrophenyl)ethanone 
• 100-52-7 benzaldehyde 
• 1222-98-6 4-nitrochalcone 
• 202341-66-0 5-(4-nitrophenyl)-3-phenyl-2-pyrazoline 
• 3672-66-0 1-(4-nitrophenyl)-3-phenylprop-2-yn-1-one 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 82231-56-9 4-(5-phenyl-1⁽²⁾H-pyrazol-3-yl)-aniline 

Relevant academic research and scientific papers

Base promoted CuFe2O4 catalyzed one-pot synthesis of 3,5-diaryl-1H-pyrazoles

Available synthetic protocols for 3,5-diaryl-1H-pyrazoles generally demand long reaction time. Herein, we are reporting a CuFe2O4 catalyzed synthetic procedure for the same that delivers products in significantly reduced time starting from tosylhydrazones of aromatic aldehydes and terminal alkynes. Under the reaction condition, tosylhydrazone generates diazo compound in situ, which then undergoes [3 + 2] cycloaddition reaction with the terminal alkyne followed by [1,3]-H shift to deliver the final products in 72%–85% isolated yield. Magnetically active CuFe2O4 nanoparticles can be recovered very easily after the completion of the reaction and can be reused up to fifth cycle without significant loss in its catalytic activity. Operational simplicity of the methodology along with tolerability of various functional groups as well as easy recovery and high reusability of CuFe2O4 nanoparticles make the procedure a practical and handy one for the synthesis of 3,5-diaryl-1H-pyrazoles.

Synthesis and theoretical study of a series of 3,5-disubstitutes pyrazoles

In this work, we proposed the synthesis of a series of pyrazoles derivatives with different substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic methodology, Density Functional Theory (DFT) calculations were performed. The reaction Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some selected reactants could explain qualitatively the experimental observations in terms of synthesis yield. In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity of the starting materials as well as the formation of the desired products.

Fast and Efficient Continuous Flow Method for the Synthesis of Ynones and Pyrazoles

In this study, we developed a convenient and efficient two-step method for the synthesis of ynones in a flow reactor, through the generation of lithium acetylide and its subsequent reactions with acid chlorides. Using this approach, we obtained the ynones in moderate to good yields at room temperature. Moreover, we transformed the ynones into pyrazole derivatives through coupling with hydrazines. This transition metal-free process, mild reaction conditions, and broad functional group tolerance are all attractive features in comparison with conventional bench-top methods.

Copper-Promoted Oxidative Intramolecular C–H Amination of Hydrazones to Synthesize 1H-Indazoles and 1H-Pyrazoles Using a Cleavable Directing Group

A facile and efficient synthesis of 1H-indazoles and 1H-pyrazoles through a copper-promoted oxidative intramolecular C–H amination of hydrazones using a cleavable directing group was developed. This reaction is characterized by its mild conditions, operational simplicity, readily available reagents, and excellent yields. A tentative mechanism for Cu-mediated C–H oxidative amination was proposed.

Sunlight-promoted Direct Irradiation of N-centred Anion: The Photocatalyst-free Synthesis of Pyrazoles in Water

A practical method through sunlight mediated annulation of α,β-unsaturated hydrazones has been developed for the synthesis of pyrazole. Based on the analysis of UV-Vis absorption of the substrate, the reaction was designed to avoid the use of external photocatalysis and proceeds via direct irradiation of N-centred anion by sunlight. The key features of this reaction include operational simplicity, readily available reagents, and amenability to gram-scale synthesis. (Figure presented.).

Iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate: Synthesis of 3,5-disubstituted 1H-pyrazoles

We have developed an iron(III) phthalocyanine chloride-catalyzed oxidation-aromatization of α,β-unsaturated ketones with hydrazine hydrate. Various 3,5-disubstituted 1H-pyrazoles were obtained in good to excellent yields. This method offers several advantages, including room-temperature conditions, short reaction time, high yields, simple work-up procedure, and use of air as an oxidant. The catalyst can be recovered and reused five times without loss of activity.

Sulphur promoted C(sp3)-C(sp2) cross dehydrogenative cyclisation of acetophenone hydrazones with aldehydes: Efficient synthesis of 3,4,5-trisubstituted 1H-pyrazoles

A novel strategy for the cross dehydrogenative coupling (CDC) of acetophenone hydrazones and aldehydes has been developed for the synthesis of highly substituted pyrazoles. This work, for the first time, uses elemental sulfur as a promoter as well as a hydrogen acceptor in effecting the Csp3-Csp2 bond formation via C-H activation. This journal is

One-pot synthesis of 3,5-diphenyl-1h-pyrazoles from chalcones and hydrazine under mechanochemical ball milling

A highly efficient and environmentally friendly method has been developed for facile synthesis of 3,5-diphenyl-1H-pyrazoles under mechanochemical ball-milling conditions. The advantages of short reaction time, high efficiency, no separation of in situ generated intermediate, using cheap sodium persulfate as the oxidant, together with very simple work-up procedure, make this one-pot and solvent-free protocol a green and powerful alternative to traditional methods for the synthesis of these kinds of compounds.

Synthesis of pyrazoles through copper-catalyzed three-component coupling of aldehydes, alkynes, and p-toluenesulfonylhydrazide

A convenient one-pot synthesis of 3,5-disubstitued 1H-pyrazoles through copper-catalyzed three-component coupling of aldehydes, alkynes, and p-toluenesulfonylhydrazide has been developed. This method provides a flexible and rapid route to 3,5-disubstituted 1H-pyrazoles.

3,5-Diaryl-1H-pyrazole as a molecular scaffold for the synthesis of apoptosis-inducing agents

The scaffold of 3,5-diaryl-1H-pyrazole was selected as a molecular template to synthesize novel growth-inhibitory agents in the present study. Our findings suggested that analogs bearing electron-withdrawing groups on one ring while electron-donating grou