670-83-7

Basic information

• Product Name: 2,4-Diphenylimidazole
• Synonyms: 2,4-DIPHENYLIMIDAZOLE;2,4-Diphenyl-1H-imidazole;2,5-Diphenyl-1H-imidazole
• CAS NO: 670-83-7
• Molecular Formula: C₁₅H₁₂N₂
• Molecular Weight: 220.27
• EINECS: 1533716-785-6
• Product Categories: pharmacetical;Imidazol&Benzimidazole
• Mol File: 670-83-7.mol
• Article Data: 42

Chemical Properties

• Melting Point: 164-166 °C(Solv: ethanol (64-17-5))
• Boiling Point: 461.2 °C at 760 mmHg
• Flash Point: 254.7 °C
• Appearance: Allmost white crystal
• Density: 1.149 g/cm³
• Vapor Pressure: 3.01E-08mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.39±0.10(Predicted)
• CAS DataBase Reference: 2,4-Diphenylimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Diphenylimidazole(670-83-7)
• EPA Substance Registry System: 2,4-Diphenylimidazole(670-83-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 670-83-7(Hazardous Substances Data)

Usage

Uses

Used in Metalworking Fluids Industry:
2,4-Diphenylimidazole is used as a corrosion inhibitor for enhancing the performance and longevity of metalworking fluids, thereby improving the efficiency of metal processing and reducing the risk of corrosion-related issues.
Used in Photopolymer Plate Production:
In the printing industry, 2,4-Diphenylimidazole serves as a stabilizer in the production of photopolymer plates, ensuring the quality and stability of the plates during the exposure process.
Used in Pharmaceutical Synthesis:
2,4-Diphenylimidazole is utilized as a starting material for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Dyes and Pigments Production:
2,4-Diphenylimidazole also acts as a building block in the creation of dyes, pigments, and other organic compounds, playing a crucial role in the coloration and enhancement of various products in industries such as textiles, plastics, and inks.

InChI:InChI=1/C15H12N2/c1-3-7-12(8-4-1)14-11-16-15(17-14)13-9-5-2-6-10-13/h1-11H,(H,16,17)

Upstream product

• 582-24-1 1-phenyl-2-hydroxyethanone 
• 618-39-3 benzamidin 
• 70-11-1 α-bromoacetophenone 
• 131548-81-7 2,4-diphenylimidazoline 
• 76849-20-2 1-cyano-2,4-diphenylimidazole 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 
• 1074-12-0 phenylglyoxal hydrate 
• 100-52-7 benzaldehyde 
• 4115-15-5 3,5-diphenyl-[1,2,4]thiadiazole 
• 1078739-19-1 1-[(4-methylphenyl)sulfonyl]-2,4-diphenyl-1H-imidazole 
• 39784-29-7 trans-1-(2-phenylvinyl)-5-phenyltetrazole 
• 1145-01-3 3,5-Diphenylpyrazole 
• 670-96-2 2-Phenylimidazole 
• 591-50-4 iodobenzene 

Downstream Products

• 26665-84-9 2-(2,5-diphenyl-imidazol-4-ylidene)-3-methyl-5-phenyl-2,3-dihydro-[1,3,4]thiadiazole 
• 26665-85-0 2,5-diphenyl-4-(5-phenyl-[1,2]dithiol-3-ylidene)-4H-imidazole 
• 26665-83-8 2,5-diphenyl-4-(4-phenyl-[1,3]dithiol-2-ylidene)-4H-imidazole 
• 26665-82-7 2,5-diphenyl-4-(5-phenyl-[1,3]thiaselenol-2-ylidene)-4H-imidazole 
• 15994-89-5 1-methyl-2,5-diphenyl-1H-imidazole 
• 99876-44-5 benzoyl-1 diphenyl-2,4 imidazole 
• 86586-47-2 (2,5-diphenyl-1⁽³⁾H-imidazol-4-yl)-methanol 
• 857271-74-0 1-ethyl-2,4-diphenyl-1H-imidazole 

Relevant articles and documents

Structure-activity relationship studies on 2-heteroaryl-4-arylimidazoles NPY5 receptor antagonists

A series of 2-heteroaryl-4-arylimidazoles with potent in vitro activity at the NPY5 receptor was developed. Introduction of electron-withdrawing groups on the 4-aryl ring led to a significant improvement of in vitro potency. Several analogues from this series had anorectic activity in rodent feeding models, but were also found to have undesired behavioral effects in spontaneous locomotor activity.

Base-promoted annulation of amidoximes with alkynes: Simple access to 2,4-disubstituted imidazoles

An efficient construction of imidazole ring by a Cs2CO3-promoied annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synehetic ropte with high atom-utilieation for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Intornal alkynes can also undetgo the annulation to give 2,4,5-trisubstituted imidazoles.

Structure and Reactivity of Highly Twisted N-Acylimidazoles

A modular and efficient synthesis of highly twisted N-acylimidazoles is reported. These twist amides were characterized via X-ray crystallography, NMR spectroscopy, IR spectroscopy, and DFT calculations. Modification of the substituent proximal to the amide revealed a maximum torsional angle of 88.6° in the solid state, which may be the most twisted amide reported for a nonbicyclic system to date. Reactivity and stability studies indicate that these twisted N-acylimidazoles may be valuable, namely as acyl transfer reagents.

Nickel-Catalyzed Construction of 2,4-Disubstituted Imidazoles via C–C Coupling and C?N Condensation Cascade Reactions

A convenient Ni(II)-catalyzed C?C and C?N cascade coupling reaction was developed to directly access various 2,4-disubstituted imidazoles. The reaction scope covers a variety of aryl and aliphatic substitutions, which demonstrate moderate-to-excellent yie

Rh-Catalyzed Annulation of ortho-C?H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-c]quinazolines

A Rh-catalyzed unique and direct approach for constructing a series of 5-arylimidazo[1,2-c]quinazolines in moderate to excellent yields from simple and readily available 2-arylimidazoles and 3-phenyl-1,4,2-dioxazol-5-ones was described. This procedure pro

ZnCl2-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2 H-Azirines for the Synthesis of Imidazoles

ZnCl2-catalyzed [3 + 2] cycloaddition reaction of benzimidates and 2H-azirines has been developed. This convenient method allowed the efficient construction of a series of multisubstituted imidazoles in moderate to good yields under mild reaction conditions. This transformation exhibits good reactivity and high functional group tolerance.

Visible Light as a Sole Requirement for Intramolecular C(sp3)-H Imination

A novel, simple, and practical visible-light-mediated intramolecular α-C(sp3)-H imination of tertiary aliphatic amines containing β-O-aryl oximes leading to N-heterocycles has been developed. The reaction was performed well at rt with tolerance of some functional groups. Importantly, the selective C-H functionalization did not require added catalyst, oxidant, additive, acid, and base; visible light was the sole requirement.

IEDDA Reaction of the Molecular Iodine-Catalyzed Synthesis of 1,3,5-Triazines via Functionalization of the sp3 C-H Bond of Acetophenones with Amidines: An Experimental Investigation and DFT Study

The present work reports an inverse electron demand Diels-Alder (iEDDA)-type reaction to synthesize 1,3,5-trizines from acetophenones and amidines. The use of molecular iodine in a catalytic amount facilitates the functionalization of the sp3 C-H bond of acetophenones. This is a simple and efficient methodology for the synthesis of 1,3,5-triazines in good to excellent yields under transition-metal-free and peroxide-free conditions. The reaction is believed to take place via an in situ iodination-based oxidative elimination of formaldehyde. DFT calculations at the M062X/6-31+G(d,p) level were employed to investigate the reaction mechanism. Reaction barriers for the cycloaddition as well as a formaldehyde expulsion steps were computed, and a multistep mechanism starting with the nucleophilic attack by benzamidine on an in situ generated imine intermediate has been proposed. Both local and global reactivity descriptors were used to study the regioselectivity of the addition steps.

Oxalyl Boronates Enable Modular Synthesis of Bioactive Imidazoles

Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized.

One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using N-Bromosuccinimide

N-bromosuccinimide (NBS)-mediated one-pot, green, efficient and practical synthesis of substituted imidazoles and quinoxalines has been achieved by the reaction of styrenes with N-arylbenzamidines and o-phenylenediamines, respectively, in a water:1,4-dioxane mixture. The reaction involves formation of an α-bromo ketone as an intermediate in the presence of NBS and water, followed by condensation with the N-arylbenzamidine and o-phenylenediamine. Use of an inexpensive NBS as a bromine source as well as an oxidant, water as a solvent and readily available starting materials makes this protocol environmentally benign and economically viable. Substituted imidazoles and quinoxalines were obtained in good to excellent yields with wide functional group compatibility. (Figure presented.).