1707-67-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Chlorophenyl)-4,5-diphenylimidazole is used as a potential therapeutic agent for its antifungal, antibacterial, and antiparasitic activities, offering a broad spectrum of action against various pathogens.
Used in Medicinal Chemistry Research:
2-(2-Chlorophenyl)-4,5-diphenylimidazole serves as a building block in organic synthesis, contributing to the development of new drugs with improved efficacy and selectivity.
Used in Drug Development:
2-(2-Chlorophenyl)-4,5-diphenylimidazole is utilized in the design and synthesis of novel pharmaceuticals, potentially leading to the creation of new treatments for various diseases and conditions.

InChI:InChI=1/C21H15ClN2/c22-18-14-8-7-13-17(18)21-23-19(15-9-3-1-4-10-15)20(24-21)16-11-5-2-6-12-16/h1-14H,(H,23,24)

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 134-81-6 benzil 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 3179-31-5 3-mercapto-1,2,4-triazole 
• 7189-82-4 2,2'-di(ortho-chlorophenyl)-4,4',5,5'-tetraphenyl-2'H-1,2'-biimidazole 
• 10421-85-9 2-chloromandelic acid 
• 501-65-5 diphenyl acetylene 
• 100-52-7 benzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 57-13-6 urea 
• 631-61-8 ammonium acetate 

Downstream Products

• 41523-36-8 1-chloro-2-(2-chloro-phenyl)-4,5-diphenyl-1H-imidazole 
• 1169497-24-8 C₄₂H₂₆Cl₄N₄ 
• 1169497-23-7 C₄₂H₂₆Cl₄N₄ 
• 1169497-25-9 C₄₂H₂₄Cl₆N₄ 
• 7189-82-4 2,2'-di(ortho-chlorophenyl)-4,4',5,5'-tetraphenyl-2'H-1,2'-biimidazole 

Relevant academic research and scientific papers

Deep eutectic solvent for multi-component reactions: A highly efficient and reusable acidic catalyst for synthesis of 2,4,5-triaryl-1H-imidazoles

Efficient synthesis of 2,4,5-trisubstituted imidazoles has been achieved by three-component cyclocondensation of benzil or benzoin, an aldehyde, and ammonium acetate by use of an acidic catalyst. The catalyst is a deep eutectic mixture of choline chloride and oxalic acid that is non-toxic and biodegradable. Crucial advantages of this process are high yields, shorter reaction times, easy work-up, purification of products by non-chromatographic methods, and reusability of the catalyst.

Pumice-modified cellulose fiber: An environmentally benign solid state hybrid catalytic system for the synthesis of 2,4,5-triarylimidazole derivatives

In this study, we developed an instrumental hybrid catalytic system comprising cellulose fiber and volcanic pumice powder, which was applied as a suitable organic–inorganic hybrid catalyst for the synthesis of 2,4,5-triarylimidazole derivatives. High reaction yields (97%) were obtained in short reaction times (20 min) using this catalytic system. In physical terms, the high porosity of pumice provides an extremely high active surface area for electronic interactions among the components. Moreover, the most distinctive properties of this catalytic system are high biodegradability, simple separation of the catalyst, and good reusability. The natural pumice can be recovered easily using an external magnet and reused with no significant decline in the catalytic activity. The structural characteristics of this efficient catalytic system were assessed using various analytical methods.

Synthesis and properties of novel reusable nano-ordered KIT-5-N-sulfamic acid as a heterogeneous catalyst for solvent-free synthesis of 2,4,5-triaryl-1H-imidazoles

A novel silica-bonded propyl-N-sulfamic acid nanocatalyst (NHSO3H-KIT-5) supported on modified silica mesopore KIT-5 as an organic-inorganic hybrid with high specific surface area was successfully prepared. The 3-aminopropyltriethoxysilane (APTES) on KIT-5 was reacted with chlorosulfonic acid and accurately characterized by the FT-IR, XRD, SEM, EDAXS, and TGA techniques. This heterogeneous and recyclable catalyst catalyzed one pot, multicomponent condensation of benzil, aromatic aldehydes, and ammonium acetate in the presences of 0.05 g of nanocatalyst under solvent-free conditions to afford triaryl-imidazoles in excellent yields. This catalyst showed high catalytic activity under green conditions. This reaction was performed under open air conditions and required no special reaction conditions or chromatographic separation for purification.

Synthesis of polymer-supported Fe3O4 nanoparticles and their application as a novel route for the synthesis of imidazole derivatives

Abstract: Cross-linked poly(4-vinylpyridine) supported Fe3O4 nanoparticles, abbreviated as [P4-VP]-Fe3O4NPs, were easily prepared as a new magnetic polymeric catalyst and efficiently used for the synthesis of imidazole derivatives. The polymeric catalyst was characterized by using of?various techniques including field emission scanning electron microscopy, X-ray diffraction, vibrating sample magnetometry and Fourier transform infrared spectroscopy (FT-IR) techniques. According to the obtained results, good dispersion of Fe3O4 nanoparticles on the polymer-support and excellent magnetic property of the catalyst were achieved. Various methods have been reported for the synthesis of multi-substituted imidazoles by the reaction of benzil, aldehydes and amines or ammonium acetate in the presence of various catalysts. These methods have some disadvantages including long reaction times, non-reusability of the catalyst, polluted reaction conditions, effluent pollution, and low yields; therefore, we wish to report an efficient, fast, clean and green method for the synthesis of imidazole derivatives that has been developed by one-pot condensation reaction of benzil, ammonium acetate and aldehydes in the presence of [P4-VP]-Fe3O4 nanoparticles. The catalyst displayed good catalytic activity when applied for the synthesis of imidazole derivatives. Various imidazole derivatives were prepared in high to excellent yields (68–99%) with short reaction time and high purity. The present procedure offers advantages such as short reaction time, simple reaction work-up, and the polymeric catalyst can be regenerated and reused several times without significant loss of its activity. Graphical abstract: [Figure not available: see fulltext.].

Sodium bisulfite as an efficient and inexpensive catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzil or benzoin and aromatic aldehydes

2,4,5-Triaryl-1H-imidazoles were efficiently synthesized from benzoin or benzil, ammonium acetate, and aromatic or heteroaromatic aldehydes in the presence of sodium bisulfite as catalyst. The present protocol offers significant improvements for the synthesis of 2,4,5-triaryl-1H-imidazoles with regard to yield of products, simplicity in operation, and cheap catalyst.

MCM-41 mesoporous silica: Efficient and reusable catalyst for the synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions

A simple, high-yielding synthesis of 2,4,5-trisubstituted imidazoles from 1,2-diketone/1,2-hydroxyketone and aldehydes in the presence of NH 4OAc is described. Under solvent-free conditions, aryl and heteroaryl substituted imidazoles are formed in yields ranging from 70 to 90%. Copyright Taylor & Francis Group, LLC.

A new nanocomposite catalyst based on clay-supported heteropolyacid for the green synthesis of 2,4,5-trisubstituted imidazoles

Intercalation of cetyltrimethylammonium (CTA+) cations within the nanolayers of montmorillonite (MMT) clay followed by reaction with Keggin-type phosphomolybdic acid (PMo) resulted in the synthesis of (CTA)3PMo-MMT nanocomposite catalyst. The prepared nanocomposite catalyst was characterized using different physicochemical methods such as Fourier-transform infrared and inductively coupled plasma–optical emission spectroscopies, X-ray diffraction, and nitrogen adsorption–desorption (Brunauer–Emmett–Teller method) analyses. Characterization techniques demonstrated the intercalation of (CTA)3PMo species into the nanolayers of MMT. The resulting (CTA)3PMo-MMT nanocomposite catalyst efficiently catalyzed the synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions. The efficiency is due to the fact that the presence of CTA+ species makes the nanocomposite catalyst hydrophobic and facilitates the accessibility of hydrophobic reactants to active sites in the course of the reaction. High activity and selectivity were achieved in the presence of the prepared nanocomposite catalyst. The nanocomposite catalyst was readily isolated from the reaction mixture using simple filtration, washed with ethanol, and recycled five times without a major loss of activity.

Ionic liquid [EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles

The ionic liquid 1-ethyl-3-methylimidazole acetate ([EMIM]OAc) was found to be a mild and effective catalyst for the efficient, one-pot, three-component synthesis of 2-aryl-4,5-diphenyl imidazoles at room temperature under ultrasonic irradiation. This procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, reacting at room temperature, high yields, simplicity of the methodology.

Sulfamic acid as an efficient and cost-effective catalyst for the synthesis of 2,4,5-triarylimidazoles and 2-arylphenanthrimidazoles

A simple and efficient synthesis of 2,4,5-triarylimidazoles and 2-arylphenanthrimidazoles was developed using the onepot, three-component condensation reaction of an aromatic aldehyde, benzil or 9,10-phenanthroquinone and ammonium acetate in refluxing ethanol in the presence of the catalyst sulfamic acid. 2011 · Copyright by Walter de Gruyter.

One-pot synthesis of 2,4,5-trisubstituted imidazoles using MoO 3/SiO2, an efficient and recyclable catalyst

A simple one-pot synthesis has been developed for the synthesis of 2,4,5-trisubstituted imidazoles using an efficient and recyclable MoO 3/SiO2 solid acid catalyst by condensation of benzil or benzoin, benzaldehyde, and ammonium acetate in acetonitrile as a solvent. Using this solid catalyst, the reactions could be carried out under mild reaction conditions with very good yield of imidazoles, up to 95%. This catalyst could be recycled very easily, which makes this methodology environmentally benign.