1750-92-1

Usage

Structure

A five-membered imidazole ring with three carbon atoms, two nitrogen atoms, and a phenyl group attached to the imidazole ring

Aromaticity

The presence of the phenyl group confers aromaticity to the compound

Reactivity and physical properties

The phenyl group influences the compound's reactivity and physical properties

Uses

Commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Applications

Potential applications in medicinal chemistry, drug development, and materials science.

Upstream product

• 74739-64-3 [1-Aziridin-1-yl-meth-(E)-ylidene]-phenyl-amine 
• 111154-10-0 N-(2-(phenylamino)ethyl)formamide 
• 1664-40-0 N-(2-aminoethyl)benzeneamine 
• 1197040-29-1 phenyl isocyanate 
• 75-52-5 nitromethane 
• 288-32-4 1H-imidazole 
• 98-80-6 phenylboronic acid 
• 74739-65-4 [1-Aziridin-1-yl-meth-(Z)-ylidene]-phenyl-amine 
• 62-53-3 aniline 

Downstream Products

• 50800-56-1 5-(4-bromophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo<2,1-a>isoindole 
• 64469-32-5 N-methyl-N'-phenyl-1,2-ethanediamine 

Relevant academic research and scientific papers

Phosphorescent Cyclometalated Platinum(II) Imidazolinylidene Complexes

We present the synthesis and characterization of six novel bidentate (Formula presented.) cyclometalated platinum(ii) complexes derived from saturated N-heterocyclic carbene precursors, namely 1-aryl-3-methyl-1H-4,5-dihydroimidazolium salts. The title compounds were then synthesized by a multi-step reaction, which includes an in situ generation of the silver carbene complex, followed by transmetalation to platinum and subsequent introduction of the β-diketonate ligand. Structural characterization by NMR experiments and solid-state structures prove the cyclometalation and the saturated backbone of the NHC motif. Photophysical and electrochemical properties of the platinum(ii) complexes were examined and studied in detail by DFT calculations. The title compounds are strongly emissive at room temperature in the sky-blue region of the visible spectrum and show quantum yields of up to 71 % in a PMMA matrix.

Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines

A novel synthetic methodology for the assembly of imidazolines via an unusual reaction between nitroalkanes and aliphatic 1,2-diamines in the presence of phosphorous acid is described. In contrast to the related highly efficient preparation of benzimidazoles from aromatic amines, this process represents a major synthetic challenge and for a long time was elusive. Analysis of the method limitations is provided.

Spherical CuO Nanoparticles as Catalyst for Chan–Lam Cross-Coupling Reaction under Base Free Condition

Abstract: An easy methodology has been developed for the N-arylation of imidazole with arylboronic acid in absence of base and ligand with the aid of as-synthesized CuO nanoparticles. The CuO nanoparticles have been synthesized via precipitation route. The as-synthesized copper oxide nanoparticles are well characterized by various analytical and spectroscopic techniques, such as powder XRD, Raman spectroscopy, TEM and BET surface area analyses. The CuO nanoparticles appear as spherical in shape with a surface area of 15.4?m2/g. The mentioned reaction successfully proceeds at moderate temperature in presence of the as-synthesized nanoparticles. The protocol is applicable to a wide variety of electronically diverse precursor moieties signifying its well applicability.

Synthesis and study of 1-aryl-1H-4,5-dihydroimidazoles

An easy synthesis of 1-aryl-1H-4,5-dihydroimidazoles 1 by cyclocondensation of N-aryl-N′-formylethylenediamines 2 is described. Such precursors were synthesized by selective formylation of N-arylethylenediamines 3 with p-nitrophenyl formate. Cyclizations were performed using trimethylsilyl polyphosphate. Chemical properties of compounds 1, typical of amidine system, were studied. Reaction of 1 with methyl iodide leads to the corresponding 1-aryl-3-methyl-1H-4,5-dihydroimidazolium salts 5. Reduction of dihydroimidazoles 1 with sodium cyanoborohydride provides a convenient access to N-aryl-N′-methylethylenediamines 4.

STEREOSPECIFIC FORMATION OF AMIDINES BY 1,1-ADDITION OF AMINES TO ISOCYANIDES

Addition of secondary amines to isonitriles in the presence of AgCl at low temperature gives isolable but thermodynamically unstable Z-amidines; only the more stable 6E undergoes ring expansion to the imidazoline 7.