27293-94-3

Usage

Chemical compound

5-(4-chlorophenyl)-1,3-diphenyl-1H-pyrazole

Molecular structure

Contains a central pyrazole ring surrounded by phenyl groups and a chlorophenyl group

Class

Pyrazole derivatives

Applications

Used in pharmaceutical and agrochemical industries

Biological activities

Diverse pharmacological properties

Potential uses

Development of new drugs for medical conditions

Safety precautions

Handle and use with caution, following proper protocols to prevent health hazards.

Upstream product

• 63389-22-0 5-(4-chloro-phenyl)-1,3-diphenyl-4,5-dihydro-1H-pyrazole 
• 125748-41-6 (5R,9S)-9-(4-Chloro-phenyl)-2,6,8-triphenyl-3-oxa-1,7,8-triaza-spiro[4.4]nona-1,6-dien-4-one 
• 129169-69-3 (4S,5R)-4-Benzoylamino-5-(4-chloro-phenyl)-1,3-diphenyl-4,5-dihydro-1H-pyrazole-4-carboxylic acid 
• 16616-42-5 p-chlorobenzoylphenylacetylene 
• 100-63-0 phenylhydrazine 
• 29776-35-0 1-(4-chlorophenyl)-3-phenylprop-2-yn-1-one 
• 24721-26-4 4-chlorochalcone 
• 591-50-4 iodobenzene 
• 536-74-3 phenylacetylene 
• 15601-44-2 (Z)-2-phenyl-4-(4-chlorobenzylidene)-5(4H)-oxazolone 
• 6969-01-3 phenyl-3-(4-chlorophenyl)oxiran-2-ylmethanone 
• 1380819-50-0 C₂₁H₁₇ClN₂ 
• 89144-71-8 4-chlorochalcone phenylhydrazone 
• 2168-78-7 methyl dithiobenzoate 

Relevant academic research and scientific papers

Cycloaddition of Nitrile Imines with Enamides: An Approach to Functionalized Pyrazolines and Pyrazoles

An efficient [3 + 2] cycloaddition of in situ generated nitrile imines with enamides has been established. A wide range of functionalized pyrazoline derivatives (53 examples) were obtained in moderate to good yields (up to 96%) under very mild conditions. This protocol features broad substrate scope, good functional group tolerance, and operational simplicity. Practical transformation of the products into useful pyrazoles via a one-pot process and the scalability of this protocol highlight the utility of this synthetic methodology.

Photooxidation of 3,5-diaryl-1-phenyl-2-pyrazolines: Experimental and computational studies

Photooxidation of various 2-pyrazolines is studied experimentally and computationally. Experimental results show that the electron-donating/withdrawing substituents increases/decreases the rate of this photoreaction. The proposed light-induced electron-tr

Visible light mediated metal-free oxidative aromatization of 1,3,5-trisubstituted pyrazolines

The visible light mediated oxidation of 1,3,5-trisubstituted pyrazolines under metal-free conditions was developed. Various substituted pyrazolines were oxidized to pyrazoles by irradiation with visible light/sunlight. A plausible mechanism was proposed f

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.

13C NMR spectroscopy of heterocycles: 1-phenyl-3-aryl/t-butyl-5-arylpyrazoles

A series of chalcones 1-12 were converted to pyrazolines (1Pi-12Pi) by reaction with phenylhydrazine followed by DDQ oxidation to produce the corresponding pyrazoles (1Pz-12Pz). Three 1-phenyl-3-t-butyl-5-arylpyrazoles (13Pz-15Pz) were synthesized using an analogous approach. Molecular modeling studies predicted the 5-aryl group of the pyrazoles for both series to have a torsion angle of 52°-54° whereas the 1-phenyl group was predicted to have 35°-37° torsion angles. The 3-aryl group was predicted to be essentially coplanar (-3°) with the pyrazole system in the first series. 13C NMR data for both series, 1Pz-12Pz and 13Pz-15Pz, were collected in DMSO-d6 at 50°C. A plot of the C4 chemical shifts for 1Pz-12Pz versus Hammet constants for 5-aryl substituents yielded a very good linear correlation (R2=0.96) with a slope of 1.5. The chemical shift data for C4 showed little or no dependence on 3-aryl substituents. The result for 13Pz-15Pz, despite only three points, was consistent with the first series results and yielded a ρ value of 2.0. Distal transmission of substituent effects (5-aryl groups) to C4 of the pyrazole system was reduced by roughly 50-60% of that of the analogous planar isoxazole system, but are not consistent with results for the similarly twisted 4-bromoisoxazoles.

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.

Synthesis and anticancer activity of 1,3,5-triaryl-1H-pyrazole

Previous studies demonstrated that some pyrazole derivatives could be considered as potential anticancer agents. A series of 1,3,5-triaryl-1H-pyrazole derivatives were prepared by the reaction of phenylhydrazin and different chalcones. The previous classi

SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H

Cathepsins have emerged as potential drug targets for melanoma therapy and engrossed attention of researchers for development and evaluation of cysteine cathepsin inhibitors as cancer therapeutics. In this direction, we have designed, synthesized, and ass

3,4-Dihydro-2H-pyran promoted aerobic oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines

An unprecedented facile oxidation of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines (DHPs) to the corresponding pyrazoles and pyridines was observed, mediated by 3,4-dihydro-2H-pyran in air. The reaction showed excellent reactivity, functional group tolerance, and high yield without using any metal and/or halogen based oxidizing agents.