384367-29-7

Basic information

• Product Name: 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl)‐2‐ethoxyphenol
• Synonyms: 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl)‐2‐ethoxyphenol
• CAS NO: 384367-29-7
• Molecular Weight: 356.424
• Mol File: 384367-29-7.mol

Chemical Properties

• CAS DataBase Reference: 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl)‐2‐ethoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl)‐2‐ethoxyphenol(384367-29-7)
• EPA Substance Registry System: 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl)‐2‐ethoxyphenol(384367-29-7)

Safety Data

• Hazardous Substances Data: 384367-29-7(Hazardous Substances Data)

Upstream product

• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 134-81-6 benzil 
• 57-13-6 urea 
• 119-53-9 2-hydroxy-2-phenylacetophenone 

Relevant articles and documents

Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

The low-melting mixture urea-ZnCl 2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1 H -imidazoles or 2-aryl-1 H -phenanthro[9,10- d ]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.

Organocatalyzed Solvent Free and Efficient Synthesis of 2,4,5-Trisubstituted Imidazoles as Potential Acetylcholinesterase Inhibitors for Alzheimer's Disease

The catalytic potential of pyridine-2-carboxlic acid has been evaluated for efficient, green and solvent free synthesis of 2,4,5-trisubstituted imidazole derivatives 3a–3m. The compounds 3a–3m were synthesized by one pot condensation reaction of substituted aromatic aldehydes, benzil, and ammonium acetate in good to excellent yields (74–96 %). To explore the potential of these compounds against Alzheimer's disease, their inhibitory activities against acetylcholinesterase (AChE) were evaluated. In this series of compounds, compound 3m, bearing one ethoxy and a hydroxy group on the phenyl ring on 2,4,5-trisubstituted imidazoles, proved to be a potent AChE inhibitor (102.56±0.14). Structure–activity relationship (SAR) of these compounds was developed. Molecular dockings were carried out for the compounds 3m, 3e, 3k, 3c, 3a, 3d, 3j, and 3f in order to further investigate the binding mechanism. The inhibitor molecule was molecularly docked with acetylcholinesterase to further study its binding mechanism. The amino group of the compound 3m forms an H-bond with the oxygen atom of the residue (i. e., THR121) which has a bond length of 3.051 ?.

Citrate trisulfonic acid: A heterogeneous organocatalyst for the synthesis of highly substituted Imidazoles

Citrate trisulfonic acid (CTSA), as a novel recyclable and eco-benign organocatalyst, was employed for the efficient and one-pot synthesis of trisubstituted imidazoles and tetrasubstituted imidazoles using aldehydes, ammonium acetate or aniline, and benzoin, benzyl, or 9,10-phenanthrenequinone under solvent-free conditions providing high to excellent yields. CTSA is easily prepared via the reaction of trisodium citrate and chlorosulfonic acid in high purity. Compared to the conventional procedures, the present method offers several advantages, including high yields, easy work-up, short reaction time, reusability of the catalyst, and simple purification of the products.

Sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles: a high-loaded and magnetically separable acid catalyst for multicomponent reactions

Abstract: In this study, a PVAm-bearing SO3H groups/Fe3O4 nanocomposite was prepared via a simple and in situ polymerization of acrylamide onto the surface of magnetic nanoparticles without using organosilane precursors. In order to obtain amine-functionalized magnetic, Hofmann degradation was carried out. In the following, sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles was prepared by covalent grafting of chlorosulfonic acid on amine groups. The introduction of polymer to the surface of magnetic nanoparticles increases the loading content with functional groups extremely. The resulting hybrid material was effectively employed as an unprecedented acid magnetic catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions. High yields, mild reaction conditions, short reaction times, operational simplicity with reusability are the notable features of the catalyst. The structure of the newly developed catalyst was characterized using TGA, FT-IR, SEM, TEM, VSM, EDX, CHNS, and XRD analysis. Magnetic separation and recycling of the catalyst for at least 8 runs is possible without any significant deterioration in catalytic activity. This work is the first report of employing PVAm as a linker for immobilizing liquid acid on a support.

Synthesis and characterization of nano-copper ferrite as a magnetically separable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free condition

The authors report herein, synthesis and characterization of nano-copper ferrite as a recoverable, ecofriendly, inexpensive, and readily available catalyst for efficient, simple, and green synthesis of multisubstituted imidazoles. Short reaction times, high yields, easy workup, and mild condition are the advantages of this protocol. The catalyst can be reused without evident loss of the catalytic activity. Characterization of the catalyst was performed fully by Fourier transform infrared spectra, X-ray diffraction, FESEM, electron dispersive X-ray, and vibration sampling magnetometer analyses.

A waste to wealth approach through utilization of nano-ceramic tile waste as an accessible and inexpensive solid support to produce a heterogeneous solid acid nanocatalyst: To kill three birds with one stone

Regarding the subject of waste products/materials, recycling or reusing has had a pivotal role on account of environmental and economic reasons. As a consequence, the essential task, nowadays, can be invention of new and practical pathways to reuse or even recycle them. In this framework, until now, recycling of some waste products such as tile wastes has not been taken into consideration; so, we were prompted by the possibility of recycling tile wastes in the catalytic direction. To this end, we use them as cost-effective, available, and nontoxic support materials for the heterogenization of sulfuric acid, in order to prepare the novel nano-ceramic tile waste supported sulfonic acid catalyst (nano-ceramic tile waste-SO3H or n-CTW-SA). This solid acid catalyst was well characterized through FT-IR, XRD, FE-SEM, EDX, TEM, TGA, BET, BJH, pH analysis and Hammett acidity function. The as-prepared nano-ceramic tile waste supported sulfonic acid catalyst proved to be an active heterogeneous catalyst in multicomponent reactions (MRCs) for the rapid and efficient one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in high yields and selectivity. In comparison with some other homogeneous and heterogeneous catalysts, nano-ceramic tile waste supported sulfonic acid displayed a greater activity. Moreover, being highly stable, inexpensive, accessible, retrievable, reusable, and having low toxicity are some other beneficial points of this catalyst.

Multi-component synthesis of highly substituted imidazoles catalyzed by nanorod vanadatesulfuric acid

Nanorod vanadatesulfuric acid (VSA NRs), as a recyclable and eco-benign catalyst, was used for one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles using aldehydes, benzil, benzoin or 9,10-phenanthrenequinone and ammonium acetate or aniline under solvent-free conditions providing high to excellent yields. VSA is easily prepared by a simple reaction of chlorosulfonic acid and sodium metavanadate in high purity. As compared with the conventional procedures, the present protocol offers several advantages such as simplicity of procedure, short reaction time, high yields, easy workup, recoverability and reusability of the catalyst and simple purification of the products.

Perlite: A cheap natural support for immobilization of sulfonic acid as a heterogeneous solid acid catalyst for the heterocyclic multicomponent reaction

Perlite sulfonic acid (Perlite-SO3H (PeSA)) has been synthesized by grafting the sulfonic groups on the perlite surface as naturally and cheap support to produce novel heterogeneous reusable solid acid catalysts. FT-IR, XRD, SEM, TGA, pH analysis and Hammett acidity function were employed to characterize the properties of the synthesized PeSA. Significantly, the as-prepared PeSA exhibits a high catalytic activity in multicomponent reaction for the one-pot synthesis of heterocyclic compound such as 3,4-dihydropyrimidin-2(1H)-ones, 2,4,5-trisubstituted imidazoles, coumarins and bis(indolyl)methanes. Additionally, the newly synthesized heterogeneous solid acid catalyst can be reused for several times without apparent loss of its catalytic activity, confirming the stability of the covalent bonding of acidic centers. PeSA has advantages such as low cost, ease of preparation, more stability and reusability, low toxicity and ease of handling.

Perlite: An inexpensive natural support for heterogenization of HBF4

Nano-perlite-fluoroboric acid (n-PeFBA) has been synthesized by immobilization of HBF4 on perlite to produce an efficient green heterogeneous reusable solid acid catalyst. The catalyst was characterized by (FE-SEM, EDX, BET and BJH). This catalyst was employed to prepare biologically important 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles with high yields and selectivities. Advantages of solid acid include: low cost, facile handling, simple preparation, high stability, reusability and low toxicity. The catalyst could be recovered and reused for several runs without deterioration in catalytic activity.

An efficient and novel one-pot synthesis of 2,4,5-triaryl-1H-imidazoles catalyzed by UO2(NO3)2.6H2O under heterogeneous conditions

An efficient, convenient, and novel one-pot method of 2,4,5-triaryl-1H- imidazoles synthesis using benzil, arene carbaldehydes, and ammonium acetate, catalyzed by uranyl nitrate hexahydrate [UO2(NO3) 2.6H2O] sup