5496-32-2

Basic information

• Product Name: 2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer
• Synonyms: 2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer;2-(2-CHLOROPHENYL)-4,5-DIPHENYLIMIDAZOLE-1,2''-DIMER, 99+%;2-(4-Chlorophenyl)-4,5-diphenyliMidazole;2-(p-Chlorophenyl)-4,5-diphenylimidazole
• CAS NO: 5496-32-2
• Molecular Formula: C₂₁H₁₅ClN₂
• Molecular Weight: 659.617
• Mol File: 5496-32-2.mol

Chemical Properties

• Melting Point: 234-236 °C (decomp)
• Boiling Point: 534.8 °C at 760 mmHg
• Flash Point: 307.8 °C
• Appearance: /
• Density: 1.23 g/cm³
• PKA: 11.26±0.10(Predicted)
• CAS DataBase Reference: 2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer(5496-32-2)
• EPA Substance Registry System: 2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer(5496-32-2)

Safety Data

• Hazardous Substances Data: 5496-32-2(Hazardous Substances Data)

Usage

Uses

Used in Forensic Science:
2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer is used as a luminescent agent for detecting bloodstains at crime scenes. It is effective in identifying trace amounts of blood due to its reaction with the iron in hemoglobin, which produces a bright blue glow. This property is crucial for uncovering evidence that may otherwise be invisible to the naked eye.
Used in Chemical Analysis:
In the field of chemical analysis, 2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer serves as a reagent that aids in the detection and measurement of specific chemical compounds, particularly those containing iron. Its sensitivity to trace amounts of substances makes it a valuable tool in various analytical processes.
Used in Environmental Monitoring:
2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer is utilized as a monitoring agent in environmental applications to detect the presence of blood or other organic materials that may indicate contamination or the presence of certain species. Its ability to react with specific compounds makes it a useful tool for ecological studies and environmental assessments.
Used in Medical Diagnostics:
In medical diagnostics, 2-(2-Chlorophenyl)-4,5-diphenylimidazole-1,2'-dimer is employed as a diagnostic aid for detecting blood in various samples, such as urine or cerebrospinal fluid. Its sensitivity to trace amounts of blood can help in the early detection of conditions like hemolysis or internal bleeding, which may not be otherwise apparent.

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 134-81-6 benzil 
• 501-65-5 diphenyl acetylene 
• 873-76-7 para-Chlorobenzyl alcohol 
• 7138-34-3 p-chloromandelic acid 
• 631-61-8 ammonium acetate 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 57-13-6 urea 
• 24242-77-1 α-iodo-α-phenylacetophenone 
• 451-40-1 phenyl benzyl ketone 
• 37580-81-7 1,2-bis(4-chlorophenyl)-1,2-ethandiol 

Downstream Products

• 3114-52-1 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 
• 55864-14-7 sodium salt of 1-(2-carboxyethyl)-2-(p-chlorophenyl)-4,5-diphenylimidazole 

Relevant articles and documents

Design, preparation and characterization of urea-functionalized Fe3O4/SiO2 magnetic nanocatalyst and application for the one-pot multicomponent synthesis of substituted imidazole derivatives

Novel urea-functionalized silica-based magnetite hybrid core-shell nanoparticles were prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX), scanning electron microscopy (SEM), X-ray diff

A green and simple method for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives using acidic ionic liquid as an effective and recyclable catalyst under ultrasound

Abstract: In the current work, an acidic ionic liquid ([{(IMC)-4-OMBH}BIM][HSO4]3) has been utilized as an effective and recyclable catalyst for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives with high yields under optimal reaction conditions and ultrasound irradiation. Important features of the new catalyst are facile synthesis, cheap reagents and successful reuse for many times. What makes the present method an effective contribution in the field of synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives is the fact that it can be described as environmentally friendly, economical, short reaction time, possible recover of the catalyst, simple workup, safer and mild reaction conditions. Graphic abstract: [Figure not available: see fulltext.].

Facile synthesis of imidazoles by an efficient and eco-friendly heterogeneous catalytic system constructed of Fe3O4 and Cu2O nanoparticles, and guarana as a natural basis

In this study, an efficient hybrid nanocatalyst made of guar gum (guarana, as a natural basis), magnetic iron oxide nanoparticles, and copper(I) oxide nanoparticles (Cu2O NPs) is fabricated and suitably applied for catalyzing the multicomponent (three- and four-component) synthesis reactions of imidazole derivatives. Here, an easy preparation strategy for this novel catalytic system (Cu2O/Fe3O4@guarana) is presented. Then, the application of this catalytic system for the synthesis of imidazole derivatives is precisely investigated. For this purpose, ultrasonication is introduced as an efficient and fast method. In summary, the high catalytic efficiency of Cu2O/Fe3O4@guarana nanocomposite is well demonstrated by high reaction yields obtained in the presence of a small amount of this nanocomposite, under mild conditions. Wide active surface area, substantial magnetic behavior, excellent heterogeneity, suitable stability, well reusability, and etc. have distinguished this catalytic system as an instrumental tool for facilitating the complex synthetic reactions.

Fe3O4@THAM-Pd as a highly efficient magnetically recoverable nanocatalyst for facile one-pot assembly of substituted imidazoles under solvent-free conditions

The current work has been explored an expeditious tactic toward one-pot multicomponent synthesis of 1,2,4,5-tetrasubstituted and 2,4,5-trisubstituted imidazoles using Fe3O4@THAM-Pd MNPs as an effective catalyst. With readily accessible benzil, ammonium acetate, anilines, and aromatic aldehydes as the simple starting materials, the condensation is run under solvent-free conditions to afford the target products in high yields. The other salient features of the present catalytic system are a simple work-up process, shorter reaction times, ease of preparation and handling of the catalyst, and cleaner reaction profiles. In addition, the sustainability of the methodology was checked by the investigation of the stability and reusability of the catalyst using an external magnet. The results showed that Fe3O4 @THAM-Pd MNPs can be reused for successive five runs without an appreciable decline in catalytic efficiency.

Magnetic nanoparticle-supported sulfonic acid as a green catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions

In this work, magnetic nanoparticle-supported sulfonic acid (γ-Fe2O3-SO3H) is used as an efficient catalyst in the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in a short time (40-70 min for trisubstituted imidazoles and 30-40 min for tetrasubstituted imidazoles) and high-purity products were obtained (92-98% for trisubstituted imidazoles and 94-98% for tetrasubstituted imidazoles) in simple multicomponent reactions. The structure of these products was confirmed via FT-IR and NMR. Green and recyclable catalysts, eco-friendly and solvent-free conditions, high catalytic activity, shorter reaction time, easy recovery by an external magnet, high purity, and excellent yields are some features of these reactions.

Magnetic horsetail plant ash (Fe3O4@HA): a novel, natural and highly efficient heterogeneous nanocatalyst for the green synthesis of 2,4,5-trisubstituted imidazoles

Horsetail plant ash (HA), as a natural source of mesoporous silica, has been prepared from the exposure of horsetail plant (Equisetum Arvense) to high temperature. In the present study, a new magnetically separable and also recoverable Fe3O4 nanoparticles were synthesized in the presence of natural horsetail plant ash (HA) as a support to result in Fe3O4@HA. FT-IR, XRD, TEM, SEM–EDX and VSM analysis were combined to characterize the morphology and structure of this novel synthesized nanocatalyst. This magnetically solid acid nanocatalyst showed an excellent catalytic activity for the synthesis of 2,4,5-trisubstituted imidazoles at room temperature in aqueous media. The procedure led to corresponding products in high to excellent yields and appropriate times. Additionally, this nanocatalyst can be easily recovered by a magnetic field and reused for six other consecutive reaction runs without noticeable loss of its catalytic efficiency. Based on this study, Fe3O4@HA is found to be an efficient, magnetically separable, recyclable, and green catalyst with natural source. Graphic abstract: In this work, horsetail plant ash was used as a natural source of mesoporous silica for the synthesis of Fe3O4@HA as a highly powerful magnetically solid acid nanocatalyst, which was fully characterized using various techniques. The activity of the newly synthesized nanocatalyst was tested for the synthesis of 2,4,5-trisubstituted imidazole derivatives.[Figure not available: see fulltext.]

TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions

In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave heating and solvent-free conditions. The chemical structures of representative trisubstituted imidazoles were confirmed using X-ray single-crystal diffraction analysis. This synthetic method has several advantages including the involvement of mild Lewis acid, being metal- and additive-free, wide substrate scope with good to excellent yields and short reaction time. Furthermore, we demonstrate the application of the methodology in the synthesis of biologically active imidazole-based drugs.

Facile fabrication of porous magnetic covalent organic frameworks as robust platform for multicomponent reaction

The design of cheap yet efficient nanoporous magnetic catalysts for the environmentally benign process's widespread application is an extremely attractive, challenging chemical research field. A novel porous magnetic covalent organic framework was prepared by the condensation reaction of melamine and terephthaladehyde on the surface of 3,4-dihydroxybenzaldehyde coated magnetic Fe3O4 nanoparticles COF@Fe3O4 under hydrothermal conditions for the first time. The high surface area magnetic COF could exhibit superior catalytic activity for sustainable synthesis of trisubstituted and tetrasubstituted imidazoles and pyrroles in good to excellent yields in PEG as solvent under environmentally friendly, ambient conditions and making the overall process economical, efficient, and green. The retrievable catalyst in PEG is general and applicable to a broad substrate scope and functional group compatibility. The structure and morphology of the COF@Fe3O4 were characterized by FTIR, XRD, EDX, and SEM spectroscopy. The COF@Fe3O4 magnetic catalyst was recovered by an external magnet and used for several cycles without significant catalytic activity loss.

Homoselective synthesis of 5-substituted 1H-tetrazoles and one-pot synthesis of 2,4,5-trisubstuted imidazole compounds using BNPs@SiO2-TPPTSA as a stable and new reusable nanocatalyst

Considering the importance of tetrazole and imidazole derivatives in pharmacy, industry, and explosives, BNPs@SiO2-TPPTSA was easily prepared and used as an effective, stable, and renewable nanocatalyst for the homoselective synthesis of different 5-substituted 1H-tetrazoles and atom economic synthesis of 2,4,5-trisubstituted-1H-imidazoles in solventless conditions. BNPs@SiO2-TPPTSA was characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD), energy dispersive X-ray analysis (EDX), thermal gravimetric-differential thermal analysis (TGA-DTA), mapping, pH analysis, and Fourier transform infrared (FT-IR) techniques. Furthermore, the catalyst recycled for at least sequential five loads without a remarkable drop-in catalytic activity.

An eco-friendly, one pot synthesis of tri-substituted imidazoles in aqueous medium catalyzed by RGO supported Au nano-catalyst and computational studies

An eco-compatible, mild and operationally simple aqueous phase protocol for the synthesis of 2,4,5-trisubstituted imidazoles has been achieved with high substrate scope using supported Au nanoparticles. The catalyst can be recovered for the subsequent rea