10040-93-4

Usage

Classification

Heterocyclic aromatic organic compound It is an organic compound containing a heterocyclic ring with aromatic properties.

Derivation

Derived from imidazole The compound is based on the imidazole structure, which is a five-membered ring containing two nitrogen atoms.

Methoxy group

Attached to the phenyl ring A methoxy group (-OCH3) is present on the phenyl ring, which is connected to the imidazole ring.

Industrial applications

Pharmaceutical industry 1H-Imidazole,1-(2-methoxyphenyl)- is used in the development and production of various pharmaceutical products.

Coordination chemistry

Ligand 1H-Imidazole, 1-(2-methoxyphenyl)can act as a ligand, binding to metal ions in coordination chemistry.

Organic synthesis

Reagent The compound serves as a reagent in organic synthesis, aiding in the formation of new chemical bonds and structures.

Importance

Industrial and research settings Due to its wide range of uses and properties, 1H-Imidazole,1-(2-methoxyphenyl)- is significant in both industrial and research environments.

Upstream product

• 288-32-4 1H-imidazole 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 529-28-2 4-iodoanisol 
• 5587-42-8 imidazolyl sodium 
• 50-00-0 formaldehyd 
• 131543-46-9 Glyoxal 
• 90-04-0 2-methoxy-phenylamine 
• 578-57-4 2-bromoanisole 
• 100-66-3 methoxybenzene 
• 90-05-1 2-methoxy-phenol 
• 85630-19-9 N,N-diethyl-1-carbamyloxy-2-methoxybenzene 
• 1137-57-1 2-methoxyphenyl N,N-dimethylsulfamate 
• 40736-26-3 1-(methylsulfonyl)-1H-imidazole 

Downstream Products

• 10041-04-0 1-(2-hydroxyphenyl)-imidazole 
• 384821-29-8 bis(N-allyl-N-methyl-5'-aminomethyl-1'-methyl-1'H-2'-imidazolyl)[1''-(2''-methoxyphenyl)-1'H-2'-imidazolyl]methyl alcohol 
• 1138156-54-3 2-(di-1-adamantylphosphino)-1-(2-methoxyphenyl)-1H-imidazole 
• 1333402-81-5 1-(2-methoxyphenyl)-3-methyl-1H-imidazol-3-ium iodide 
• 1425052-90-9 2-(dicyclohexylphosphanyl)-1-(2-methoxyphenyl)-1H-imidazole 
• 1425052-92-1 2-(diisopropylphosphino)-1-(2-methoxyphenyl)-1H-imidazole 
• 1425052-93-2 2-(diphenylphosphino)-1-(2-methoxyphenyl)-1H-imidazole 

Relevant academic research and scientific papers

Bis(μ-iodo)bis((-)-sparteine)dicopper(I): versatile catalyst for direct N-arylation of diverse nitrogen heterocycles with haloarenes

The easy-to-prepare dimeric bis(μ-iodo)bis((-)-sparteine)dicopper(I) complex is shown to be a versatile catalyst for N-arylation of number of NH-heterocycles with structurally divergent aryl halides including activated aryl chloride substrates under mild conditions. The DFT studies not only provide structural insights into square-pyramidal Cu(III) intermediate complexes derived from (-)-sparteine, but also highlight the important role of sterically demanding (-)-sparteine ligand framework in promoting activation of aryl-chlorine bonds for N-arylation of imidazoles.

Cheap Cu(I)/hexamethylenetetramine (HMTA) catalytic system for C-N coupling reactions

An efficient C-N coupling reaction of aryl chlorides or bromides with imidazole was successfully performed with cheap and commercially available catalytic system Cu(I)/HMTA. Both aryl bromides and aryl chlorides have been effectively catalyzed by Cu/HMTA, giving products in moderate to good yields. Moreover, aryl halides bearing either electron-withdrawing groups or electron-donating groups could be used in the reaction. Taylor & Francis Group, LLC.

Open-air N-arylation of N-H heterocycles with arylboronic acids catalyzed by copper(II) Schiff base complexes

Two copper Schiff base complexes, in both homogeneous and heterogeneous forms, were prepared and characterized by using elemental analysis, FTIR, UV-Vis spectroscopy and scanning electron microscopy. The catalytic performances of these complexes were studied in the N-arylation of N-H heterocycles with arylboronic acids in methanol without any added base at 40 °C under open air. The effects of various parameters such as solvent and temperature on the reaction system were studied. The reaction is applicable to a wide variety of N-H heterocycles and arylboronic acids. The heterogeneous catalyst was recovered by simple filtration, and reusability experiments showed that this catalyst can be used five times without much loss in the catalytic activity.

A versatile and efficient cu-catalyzed N-Arylation of aromatic cyclic secondary amines with aryl halides

A copper-catalyzed coupling reaction of aryl halides with various aromatic cyclic secondary amines in DMSO has been developed efficiently. The versatile and efficient copper catalyst system is of wide-spread and practical application in cross-coupling reactions.

Cross coupling of arylboronic acids with imidazoles by sulfonatocopper(II) (salen) complex in water

A mild and clean protocol for the cross coupling reactions between imidazoles and arylboronic acids has been developed in good to excellent yields up to 98% in the presence of sulfonatocopper(II)(salen) catalyst in water without addition of other additives and bases.

2,6-Bis(2-methylhydrazine-1-carbonyl)pyridine 1-oxide as an Efficient Ligand for Copper-Catalyzed C–N Coupling Reaction in Water

Abstract: Cu2O/2,6-bis(2-methylhydrazine-1-carbonyl)pyridine 1-oxide was found to be an efficiently catalytic system for the N-arylation of imidazole, indole, benzimidazole, pyrrole, benzylamine and ethanolamine with aryl iodides and bromides by using NaOH as base in the presence of 20?mol% (n-Bu)4NBr, and water as solvent at 130?°C in 24?h, and giving the N-arylated products in moderate to excellent yields.

Copper(I) 3-methylsalicylate mediates the Chan-Lam N-arylation of heterocycles

Copper(I) 3-methylsalicylate (CuMeSal) mediates N-arylation reactions between aryl boronic acids and aromatic heterocycles (Chan-Lam coupling) under moderate reaction conditions (K2CO3, methanol, 65 °C, in air, 3-5 h). Both electron-rich and electron-deficient aryl boronic acids and a diverse set of N-heterocycles were allowed to react and gave N-arylation products in reasonable yields, which demonstrate the utility of this catalyst.

Cu(OTf)2-Mediated Cross-Coupling of Nitriles and N-Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products**

Metal-catalyzed C–N cross-coupling generally forms C?N bonds by reductive elimination from metal complexes bearing covalent C- and N-ligands. We have identified a Cu-mediated C–N cross-coupling that uses a dative N-ligand in the bond-forming event, which, in contrast to conventional methods, generates reactive cationic products. Mechanistic studies suggest the process operates via transmetalation of an aryl organoboron to a CuII complex bearing neutral N-ligands, such as nitriles or N-heterocycles. Subsequent generation of a putative CuIII complex enables the oxidative C–N coupling to take place, delivering nitrilium intermediates and pyridinium products. The reaction is general for a range of N(sp) and N(sp2) precursors and can be applied to drug synthesis and late-stage N-arylation, and the limitations in the methodology are mechanistically evidenced.

Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides

Benzotriazole (BtH) is an efficient ligand for the Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides. A combination of CuI/BtH was found to be an efficient and inexpensive catalyst system to carry out the N-arylation of imidazoles affording the corresponding products in good to excellent yields.

An in situ generated CuI/metformin complex as a novel and efficient catalyst for C-N and C-O cross-coupling reactions

An in situ generated complex of copper(I) and a biguanide, namely metformin, was found to be a highly efficient homogeneous catalyst in N/O-arylation reactions. The O-arylation of substituted phenols with various aryl iodides and bromides was also achieved using this copper catalyst to afford diaryl ethers in good to excellent yields in DMF. This heterogeneous copper catalyst also promotes the N-arylation of imidazole with a variety of aryl halides (Cl, Br, I) in acetonitrile.