16112-34-8

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-methylphenyl)-1,5-diphenyl-1H-pyrazole is used as a potential candidate for drug development due to its distinctive chemical structure and properties. It may contribute to the creation of new medications targeting various health conditions, pending further research and clinical trials.
Used in Materials Science:
In the field of materials science, 3-(4-methylphenyl)-1,5-diphenyl-1H-pyrazole is used as a building block for designing and synthesizing novel materials with specific characteristics. Its unique structure allows for the development of materials with tailored properties for use in various applications, subject to ongoing studies and exploration.

Upstream product

• 14802-30-3 (E)-1-(4-methylphenyl)-3-phenyl-2-propen-1-one 
• 100-63-0 phenylhydrazine 
• 104-87-0 4-methyl-benzaldehyde 
• 536-74-3 phenylacetylene 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 
• 591-50-4 iodobenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 59-88-1 phenylhydrazine hydrochloride 
• 2829-25-6 4-methylbenzaldehyde phenylhydrazone 
• 589-18-4 4-Methylbenzyl alcohol 
• 25939-01-9 p-toluoyl chloride phenylhydrazone 
• 874-60-2 4-methyl-benzoyl chloride 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

Synthesis of pyrazoles by a one-pot tandem cyclization-dehydrogenation approach on Pd/C/K-10 catalyst

A novel one-pot synthesis of substituted pyrazoles from chalcones and hydrazines via a tandem cyclization-dehydrogenation approach is described. This process is based on the use of a bifunctional noble-metal/solid-acid catalyst, Pd/C/K-10 montmorillonite

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization

Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.

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.

Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines

An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of β-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.

Method for efficiently preparing 1,3,5-trisubstituted pyrazole compound

The invention discloses a method for efficiently preparing a 1,3,5-trisubstituted pyrazole compound. According to the method for efficiently preparing the 1,3,5-trisubstituted pyrazole compound, with metal palladium as a catalyst and triethylamine as an additive, aryl hydrazide hydrochloride, terminal alkyne and carbon monoxide are used as raw materials and react with one another under a heated condition in the atmosphere of oxygen to obtain the 1,3,5-trisubstituted pyrazole compound; and the reaction formula is formula (1). The method for efficiently preparing the 1,3,5-trisubstituted pyrazole compound realizes a method for preparing the 1,3,5-trisubstituted pyrazole compound by using palladium-catalyzed one-pot multi-component cascade reaction; and the method for efficiently preparing the 1,3,5-trisubstituted pyrazole compound has the advantages of simplicity, feasibility, simply and easy obtaining of raw materials and wide application prospect.

A Regioselective Approach to Trisubstituted Pyrazoles via Palladium-Catalyzed Oxidative Sonogashira-Carbonylation of Arylhydrazines

A palladium-catalyzed oxidative carbonylation of arylhydrazines and alkynes with balloon pressure CO/O2 to afford trisubstituted pyrazoles in a one-pot manner has been developed. The formation of trisubstituted pyrazoles involves a sequential C-N bond cleavage, carbonylation, Sonogashira coupling, Michael addition, and intramolecular condensation cyclization tandem process. An unprecedented oxidative Sonogashira-carbonylation reaction of arylhydrazine plays a key role for such a facile approach to pyrazoles.

Nucleophilic ring-opening reactions of trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates with hydrazines

trans-2-Aroyl-3-aryl-cyclopropane-1,1-dicarboxylates when treated with arylhydrazines in refluxing EtOH gave dihydropyrazoles, whereas with hydrazines in refluxing AcOH, they formed cyclopropane-fused pyridazinones. Although in both cases the corresponding hydrazones are formed initially, the former case involves a subsequent 5-exo-tet nucleophilic ring-opening, and the later, a 6-exo-trig nucleophilic attack by the other hydrazone nitrogen. The products are obtained in moderate to excellent yields with complete regio-and diastereoselectivity.

Radical Addition of Hydrazones by α-Bromo Ketones to Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis

A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramolecular cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles.

Four-component synthesis of β-enaminone and pyrazole through phosphine-free palladium-catalyzed cascade carbonylation

The carbonylative domino synthesis of enaminones and pyrazoles has been performed with the N?N bidentate palladium catalyst to achieve excellent selectivity. These results have confirmed that the carbonylative Sonogashira coupling of iodobenzenes with ter