2154-38-3

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-5-PHENYL-1H-IMIDAZOLE is used as an intermediate in the production of organic synthesis and pharmaceuticals. Its biological activities, such as antimicrobial and antifungal properties, make it a promising candidate for drug development.
Used in Materials Science:
1-METHYL-5-PHENYL-1H-IMIDAZOLE is used in the construction of conducting polymers, contributing to the advancement of materials with potential applications in electronics and other industries.
Used as a Corrosion Inhibitor:
In materials science, 1-METHYL-5-PHENYL-1H-IMIDAZOLE has also been studied for its potential use as a corrosion inhibitor, which can be beneficial in protecting materials from degradation and extending their lifespan in various applications.

InChI:InChI=1/C10H10N2/c1-12-8-11-7-10(12)9-5-3-2-4-6-9/h2-8H,1H3

Upstream product

• 71333-60-3 (E)-1-Isocyano-2-phenyl-1-tosylethene 
• 74-89-5 methylamine 
• 917364-28-4 1-Methyl-5-phenyl-1H-imidazole-4-carboxylic acid 
• 87022-42-2 1-(isocyanomethyl)-1H-benzo[d][1,2,3]triazole 
• 622-29-7 N-Benzylidenemethylamine 
• 616-47-7 1-methyl-1H-imidazole 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 38036-86-1 N-acetyl-4⁽⁵⁾-phenylimidazole 
• 74-88-4 methyl iodide 
• 670-95-1 4-phenyl-1H-imidazole 
• 333-27-7 methyl trifluoromethanesulfonate 
• 1003-21-0 5-bromo-N-methylimidazole 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1111266-98-8 4-bromo-1-methyl-5-phenyl-1H-imidazole 
• 1278587-32-8 1-methyl-2-(2-pyridyl)-5-phenyl-1H-imidazole 
• 1278587-51-1 1-methyl-2,5-diphenyl-4-(1-naphthyl)-1H-imidazole 
• 36783-83-2 1-methyl-2,5-diphenyl-4-(4-nitrophenyl)-1H-imidazole 
• 22397-44-0 1-methyl-2,4,5-triphenyl-1H-imidazole 
• 15994-89-5 1-methyl-2,5-diphenyl-1H-imidazole 
• 1278587-34-0 1-methyl-2-(2-methoxyphenyl)-5-phenyl-1H-imidazole 
• 1278587-33-9 1-methyl-2-(1-naphthyl)-5-phenyl-1H-imidazole 
• 1278587-24-8 1-methyl-2-(4-methoxyphenyl)-5-phenyl-1H-imidazole 
• 1312713-38-4 C₂₄H₂₂N₂O₂ 
• 1278587-43-1 1-methyl-2-(4-methoxyphenyl)-4-(4-trifluoromethylphenyl)-5-phenyl-1H-imidazole 
• 1278587-26-0 1-methyl-2-(4-trifluoromethylphenyl)-5-phenyl-1H-imidazole 
• 1312713-40-8 C₂₄H₁₆F₆N₂ 
• 1278587-44-2 1-methyl-2-(4-trifluoromethylphenyl)-4-(4-methoxyphenyl)-5-phenyl-1H-imidazole 

Relevant academic research and scientific papers

4,5-Dihydro-imidazol-2-ylidene-linked palladium complexes as catalysts for the direct C-H bond arylation of azoles

Recently, PEPPSI-type palladium-complexes bearing N-heterocyclic carbene (NHC) ligand have commonly been used as the effective catalysts in the direct arylation of heteroaromatic compounds. In most of previous studies catalyzed by such complexes, unsatura

Method for catalyzing direct arylation of imidazole compound by using palladium complex

The invention relates to a method for catalyzing direct arylation of an imidazole compound by using a palladium complex, which comprises the following steps: in the presence of alkali, taking the imidazole compound and aryl halide as raw materials, taking

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

The heme enzyme indoleamine 2,3-dioxygenase 1 (IDO1) plays an essential role in immunity, neuronal function, and aging through catalysis of the rate-limiting step in the kynurenine pathway of tryptophan metabolism. Many IDO1 inhibitors with different chemotypes have been developed, mainly targeted for use in anti-cancer immunotherapy. Lead optimization of direct heme iron-binding inhibitors has proven difficult due to the remarkable selectivity and sensitivity of the heme-ligand interactions. Here, we present experimental data for a set of closely related small azole compounds with more than 4 orders of magnitude differences in their inhibitory activities, ranging from millimolar to nanomolar levels. We investigate and rationalize their activities based on structural data, molecular dynamics simulations, and density functional theory calculations. Our results not only expand the presently known four confirmed chemotypes of sub-micromolar heme binding IDO1 inhibitors by two additional scaffolds but also provide a model to predict the activities of novel scaffolds.

Palladium-Based Catalysts Supported by Unsymmetrical XYC–1 Type Pincer Ligands: C5 Arylation of Imidazoles and Synthesis of Octinoxate Utilizing the Mizoroki–Heck Reaction

A series of new unsymmetrical (XYC–1 type) palladacycles (C1–C4) were designed and synthesized with simple anchoring ligands L1–4H (L1H = 2-((2-(4-methoxybenzylidene)-1-phenylhydrazinyl)methyl)pyridine, L2H = N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl)aniline, L3H = N,N-diethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl) aniline and L4H = 4-(4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono) methyl)phenyl)morpholine H = dissociable proton). Molecular structure of catalysts (C1–C4) were further established by single X-ray crystallographic studies. The catalytic performance of palladacycles (C1–C4) was explored with the direct Csp2–H arylation of imidazoles with aryl halide derivatives. These palladacycles were also applied for investigating of Mizoroki–Heck reactions with aryl halides and acrylate derivatives. During catalytic cycle in situ generated Pd(0) nanoparticles were characterized by XPS, SEM and TEM analysis and possible reaction pathways were proposed. The catalyst was employed as a pre-catalyst for the gram-scale synthesis of octinoxate, which is utilized as a UV-B sunscreen agent.

Palladium Complexes of Thio/Seleno-Ether Containing N-Heterocyclic Carbenes: Efficient and Reusable Catalyst for Regioselective C-H Bond Arylation

The synthesis of the novel S,CNHC type half-pincer ligand precursors (L1 and L2) is described herein by using the atom economy reactions of 1-(2-(phenylthio)ethyl)-1H-imidazole with benzyl bromide and bromodiphenylmethane, respectively. The analogous reaction of 1-(2-(phenylselanyl)ethyl)-1H-imidazole with 2-bromoethyl phenyl sulfide has also resulted in a imidazolium bromide (L3) which is a precursor of novel S,CNHC,Se type pincer ligand. The route of silver-NHC transmetalation was employed to get the palladium complexes [Pd(L1/L2–HBr)Cl2] (C1 and C2) and [Pd(L3–HBr)Cl]BF4 (C3). The imidazolium bromide (L1–L3) and palladium complexes (C1–C3) were characterized by using multinuclear NMR and HR-MS. The structure and bonding in the complexes C1 and C2 were validated by X-ray crystallography. Thermally robust and moisture/air insensitive palladium complexes C1–C3 have been explored in the catalysis of C–H bond arylation of imidazoles. The protocol operates under mild reaction conditions in air with an excellent regioselective C–H bond arylation at C-5 position in imidazoles. All the complexes were found to be efficient (yield up to 97 % in 12 h) in the catalysis; however, the activating pincer ligand framework containing Pd catalyst C3, was found to be utmost effective among the three catalysts. Only 0.5 mol-% catalyst loading is required to achieve admirable yield of the desired cross-coupled products. A wide range of substrates was examined, and the developed protocol was applicable to all derivatives with high functional group tolerance and greater efficiency. More importantly, the catalyst C3 has also been found recyclable up to five cycles with minor decrease in efficiency which is highly desirable feature for the development of economical and sustainable industrial reaction processes. The PPh3 and Hg poisoning tests have established the complete homogeneous nature of the catalysis.

Palladium complexes of chalcogenoethanamine (S/Se) bidentate ligands: Applications in catalytic arylation of C[sbnd]H and O[sbnd]H bonds

This report describes the syntheses of N,E (E = S, Se) coordinated bidentate palladium complexes, by the reaction of N-(2-bromobenzyl)-2-(phenylthio/selanyl)ethanamine (3, 4) with [PdCl2(CH3CN)2]. The new ligands and palladium complexes were characterized by techniques like 1H, 13C{1H} NMR, IR, and elemental analysis. The coordination modes of ligand with palladium precursor in complexes 5 and 6 were authenticated by single crystal X-ray diffraction. The complexes possess distorted square planar geometry around palladium center. Thermally robust and air stable complexes 5 and 6 were used as catalyst for regioselective arylation of imidazole and O-arylation of phenol. In case of regioselective arylation of imidazole, the reaction proceeds smoothly under mild reaction conditions, only 2.0 mol% of catalyst loading is required to achieve high yield (76–92%). This protocol is applicable to a broad substrate scope showing excellent tolerance towards different functional groups. Whereas for O-arylation of phenol also only 2.0 mol% catalyst loading is sufficient to give good yield (71–92%) with excellent tolerance towards a broad range of functional groups. Among sulfur and selenium coordinated ligands, selenium ligand coordinated complex, was found to outperform the catalytic reactions in both cases as compare to sulfur ligand. The mercury and triphenylphosphine poisoning tests suggest homogeneous nature of catalysis.

3-(AZOLYLMETHOXY)BIPHENYL DERIVATIVES AS INHIBITORS OF THE PD-1/PD-L1 PROTEIN/PROTEIN INTERACTION

The present invention provides novel compounds of formula (I) that are useful as inhibitors of the PD-1/PD-L1 protein/protein interaction. The compounds may be used in the treatment of cancer, infectious diseases and neurodegenerative diseases such as schizophrenia, Alzheimer, multiple sclerosis or Parkinson.

Palladium(II) Complexes of N-Heterocyclic Carbene Amidates Derived from Chalcogenated Acetamide-Functionalized 1 H-Benzimidazolium Salts: Recyclable Catalyst for Regioselective Arylation of Imidazoles under Aerobic Conditions

The chalcogenated acetamide-functionalized 1H-benzimidazolium salt precursors [1-(CH2C(O)NH(CH2)2S/SePh)-3-R-C7H5N2]+ X (L1-L4; R = Me, CH2Ph; X = Br, I) to C,N,S/Se l

Developing Bis(imino)acenaphthene-Supported N-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles

On the basis of the strategy of developing highly efficient protocol for Pd-catalyzed cross-coupling reactions, a series of bulky bis(imino)acenaphthene (BIAN)-supported Pd-PEPPSI complexes were synthesized, characterized, and applied in direct arylation

Novel (N-heterocyclic carbene)Pd(pyridine)Br2 complexes for carbonylative Sonogashira coupling reactions: Catalytic efficiency and scope for arylalkynes, alkylalkynes and dialkynes

New N,N′-substituted imidazolium salts and their corresponding dibromidopyridine–palladium(II) complexes were successfully synthesized and characterized. Reactions of palladium bromide with the newly synthesized N,N′-substituted imidazolium bromides (2a a