32664-28-1

Basic information

• Product Name: 5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole
• Synonyms: 1H-pyrazole, 3-(4-methoxyphenyl)-5-phenyl-
• CAS NO: 32664-28-1
• Molecular Formula: C₁₆H₁₄N₂O
• Molecular Weight: 250.2952
• Mol File: 32664-28-1.mol

Chemical Properties

• Boiling Point: 472.6°C at 760 mmHg
• Flash Point: 168.8°C
• Density: 1.161g/cm³
• Vapor Pressure: 1.2E-08mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole(32664-28-1)
• EPA Substance Registry System: 5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole(32664-28-1)

Safety Data

• Hazardous Substances Data: 32664-28-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole is used as a research compound for exploring its biological activities and potential therapeutic applications. Its anti-inflammatory and anti-cancer effects make it a promising candidate for the development of new drugs targeting various diseases.
Used in Organic Synthesis:
In the field of organic chemistry, 5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole is utilized as a building block in the synthesis of other organic compounds. Its unique structure allows for the creation of novel molecules with potential applications in various industries.
Used in Medicinal Chemistry:
5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole is employed as a key intermediate in the design and synthesis of new pharmaceutical agents. Its presence in the molecular structure can influence the pharmacokinetic and pharmacodynamic properties of the resulting compounds, enhancing their therapeutic potential.
Used in Drug Discovery:
In the drug discovery process, 5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole serves as a valuable tool for identifying and optimizing lead compounds with desired biological activities. Its unique structural features can be exploited to improve the potency, selectivity, and safety of new drug candidates.
Used in Chemical Research:
5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole is utilized in chemical research to study the reactivity and properties of pyrazole derivatives. Understanding its chemical behavior can provide insights into the development of new synthetic methods and applications in various fields.

Upstream product

• 851729-18-5 3-phenyl-5-(4-methoxyphenyl)-4-hydroxy-4,5-dihydro-1H-pyrazole 
• 64-19-7 acetic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 536-74-3 phenylacetylene 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 563-41-7 semicarbazide hydrochloride 
• 18873-03-5 trans-1-p-methoxyphenyl-3-phenyl-2,3-epoxy-1-propanone 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 1427296-19-2 3-amino-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 89144-75-2 3-(4-Methoxy-phenyl)-5-phenyl-4,5-dihydro-1H-pyrazole 
• 199620-14-9 chromium⁽⁰⁾ hexacarbonyl 
• 5953-85-5 p-anisaldehyde hydrazone 
• 98-86-2 acetophenone 

Downstream Products

• 1429205-24-2 C₁₆H₁₄N₂O*HNO₃ 
• 36837-37-3 1-acetyl-3-(4-methoxy-phenyl)-5-phenyl-1H-pyrazole 

Relevant articles and documents

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.

Denitrative imino-diaza-Nazarov cyclization: Synthesis of pyrazoles

An iodine-catalyzed denitrative imino-diaza-Nazarov cyclization (DIDAN) methodology has been developed for the synthesis of pyrazoles with high to excellent yields by using α-nitroacetophenone derivatives and in situ generated hydrazones. The key transformation of this oxidative 4π-electrocyclization proceeds through an enamine-iminium ion intermediate. This rapid one-pot DIDAN protocol results in the selective generation of C-C and C-N bonds and cleavage of a C-N bond. This journal is

Heck Reactions of Acrolein or Enones and Aryl Bromides – Synthesis of 3-Aryl Propenals or Propenones and Consecutive Application in Multicomponent Pyrazole Syntheses

3-(Hetero)aryl propenals or propenones are efficiently prepared by a Heck reaction of (hetero)aryl bromides and acrolein or vinyl ketones using Beller's CataCXium Ptb ligand under Jeffery's and Fu's conditions. The formation of these three-carbon building blocks is embedded into consecutive three- and pseudo-four-component syntheses of 3-(hetero)aryl and 3,5-diarylpyrazoles with a broad substitution pattern in moderate to excellent yield.

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.

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.

An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride

An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles by simply heating pyrazolines in DMSO under oxygen.

The diaza-Nazarov cyclization involving a 2,3-diaza-pentadienyl cation for the synthesis of polysubstituted pyrazoles

An unprecedented iodine-mediated diaza-Nazarov (DAN) type cyclization for the construction of substituted pyrazoles from easily available starting materials via an enamine-iminium ion intermediate is described. The oxidative cyclization worked under green conditions with remarkable regioselectivity. This one-pot, efficient and operationally simple three-component intramolecular regioselective DAN cyclization displayed a wide range of substrate scope. The dichotomy of reaction pathways has been explored with density functional theory in the gas phase and solution phase. Of the possible 1,5-, 1,6-, and 1,7-electrocyclizations, the DAN cyclization, i.e., the 1,5-pathway offers the lowest activation energy barrier supporting our experimental observations.

Phosphine- and copper-free palladium catalyzed one-pot four-component carbonylation reaction for the synthesis of isoxazoles and pyrazoles

The palladium catalyzed one-pot synthesis of isoxazoles and pyrazoles from aryl iodides, terminal alkynes, chromium hexacarbonyl and hydroxylamine hydrochloride or aqueous hydrazine solution is described. The Sonogashira carbonylative coupling intermediate was trapped in situ by hydroxylamine hydrochloride or aqueous hydrazine to deliver isoxazoles or pyrazoles, respectively, in high yields. This efficient method proceeds at atmospheric pressure and moderate temperature and does not require the use of copper, phosphine ligands or gaseous carbon monoxide.

A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles

In the presence of 0.5 mol% of 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(OAc)2] and 1.0 mol% of CuI, acid chlorides were coupled with terminal alkynes in Et3N at 50 °C to give α,β-unsaturated ynones, which were converted in situ into pyrazoles by the cycloaddition of hydrazines at room temperature with acetonitrile as cosolvent. The cascade reactions generated a variety of pyrazole derivatives in moderate to good yields, and this heterogeneous palladium catalyst exhibited higher catalytic activity than PdCl2(PPh3)2 and could be recovered and reused for at least 10 consecutive trials without any decreases in activity.

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.