2284-96-0

Basic information

• Product Name: 2-(4-Fluorophenyl)-4,5-diphenylimidazole
• Synonyms: 2-(4-Fluorophenyl)-4,5-diphenylimidazole;2-(4-fluorophenyl)-4,5-diphenyl-1H-imidazole
• CAS NO: 2284-96-0
• Molecular Formula: C₂₁H₁₅FN₂
• Molecular Weight: 314.3556032
• EINECS: -0
• Mol File: 2284-96-0.mol
• Article Data: 70

Chemical Properties

• Melting Point: 254.0 to 258.0 °C
• Appearance: /
• CAS DataBase Reference: 2-(4-Fluorophenyl)-4,5-diphenylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Fluorophenyl)-4,5-diphenylimidazole(2284-96-0)
• EPA Substance Registry System: 2-(4-Fluorophenyl)-4,5-diphenylimidazole(2284-96-0)

Safety Data

• Hazardous Substances Data: 2284-96-0(Hazardous Substances Data)

Usage

Chemical Class

Imidazoles

Physical Form

White to off-white crystalline powder

Usage

Research and pharmaceutical applications

Anti-Cancer Properties

Demonstrated

Target Enzyme

Wip1 phosphatase

Mechanism of Action

Inhibits the enzyme, leading to the induction of apoptosis and inhibition of cancer cell growth

Potential Use

Cancer treatment

Additional Application

Fluorescent probe for zinc ion detection in biological systems

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 24133-58-2 1,2-bis(4-fluorophenyl)-1,2-ethanediol 
• 134-81-6 benzil 
• 459-56-3 4-fluorobenzylic alcohol 
• 501-65-5 diphenyl acetylene 
• 24242-77-1 α-iodo-α-phenylacetophenone 
• 451-40-1 phenyl benzyl ketone 
• 631-61-8 ammonium acetate 

Downstream Products

• 255065-89-5 [2-(4-fluoro-phenyl)-4,5-diphenyl-imidazol-1-yl]-acetic acid hydrazide 

Relevant articles and documents

Influence of Bio-Isosteric Replacement on the Formation of Templating Methanol and Acetonitrile Solvates in Lophines

Bio-isosteric replacement is a frequently used tool in medicinal chemistry. While the pharmacological activity is not influenced by the exchange of substituents, the solid-state characteristics and formation of different crystal forms may well be altered dramatically, jeopardizing the processability and safety of the drug compound. In this study we investigate a series of triphenylimidazole (TPI) derivatives as model compounds with the bio-isosteric exchange of only one halogen position (F, Cl, Br, I). Crystallization from two industrially used solvents (methanol and acetonitrile) reveals solvate formation of all TPIs, for which the basic hydrogen bonded motif does not change. The three-dimensional packing depends on the size of the substituent and changes from fluoro- to chloro- and bromo-substitution but remains the same for the larger iodo-substituent. From acetonitrile, only F-TPI and Cl-TPI form an isomorphic channel solvate, which in both cases desolvates reversibly to an isomorphic crystal form. Due to the halogen atom lining of the channels, bromine and iodine are too large to generate a stable packing. This study illustrates the importance of understanding the influence of bio-isosteric substitution on the solid state, in order to best utilize this common tool.

An Efficient and Green Synthesis of Imidazoles Using Natural Organic Acids as Promoter under Solvent-Free Condition

An efficient and eco-friendly synthesis of imidazoles, promoted by naturally occurring acids, via condensation of benzil, aldehyde and ammonium acetate using conventional and microwave heating under solvent-free condition is described. Reactions under mic

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.

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.