24641-31-4

Usage

Uses

Used in Organic Synthesis:
2-(4-Bromophenyl)quinoline is used as a building block in organic synthesis for the creation of various chemical products. The bromine atom allows for further functionalization and modification of the molecule, facilitating the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
2-(4-Bromophenyl)quinoline is used as a starting material for the synthesis of pharmaceuticals. The quinoline structure has been identified to possess biological activities, and its derivatives are being investigated for their potential use in medicine. The presence of the bromine atom on the phenyl ring may contribute to the compound's pharmacological properties, enhancing its therapeutic potential.
Used in Chemical Reactions:
2-(4-Bromophenyl)quinoline is used as a versatile starting material in various chemical reactions. The bromine atom can participate in a range of reactions, such as substitution, addition, and elimination, enabling the synthesis of diverse chemical products with different functional groups and properties. This makes the compound a valuable intermediate in the development of new chemical entities and materials.

InChI:InChI=1/C15H10BrN/c16-13-8-5-12(6-9-13)15-10-7-11-3-1-2-4-14(11)17-15/h1-10H

Upstream product

• 91-22-5 quinoline 
• 22480-64-4 4-bromophenyllithium 
• 103914-52-9 2-(4'-bromophenyl)quinoline-4-carboxylic acid 
• 99-73-0 para-bromophenacyl bromide 
• 1222458-20-9 C₁₆H₁₁BrClNO 
• 5344-90-1 2-Aminobenzyl alcohol 
• 99-90-1 para-bromoacetophenone 
• 612-25-9 2-Nitrobenzyl alcohol 
• 5391-88-8 1-(4-bromophenyl)ethanol 
• 4403-69-4 2-amino-1-benzylamine 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 552-89-6 2-nitro-benzaldehyde 
• 58106-57-3 (E)-3-(2-aminobenzene)acrylonitrile 
• 5467-74-3 4-Bromophenylboronic acid 

Downstream Products

• 1016275-42-5 (S)-2-(4-bromophenyl)-1,2,3,4-tetrahydroquinoline 
• 1312162-99-4 (R)-2-(4-bromophenyl)-1,2,3,4-tetrahydroquinoline 
• 1354658-32-4 C₂₂H₁₄BrClN₂O₃ 
• 1383803-71-1 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinoline 
• 1605333-11-6 2-(4′-(trifluoromethyl)-4-biphenyl)quinoline 
• 14251-81-1 2-(biphenyl-4-yl)quinoline 
• 1494687-58-9 2-(4-bromophenyl)-1,2,3,4-tetrahydroquinoline 
• 1220526-54-4 2-[4,4-di(2-quinolyl)-[1,1';3',1]-terphenyl-5'-yl]-4,6-di-p-tolyl-1,3,5-triazine 
• 132318-11-7 4-[2]quinolyl-benzoic acid 

Relevant academic research and scientific papers

A self-calibrating phosphorescent polymeric probe for measuring pH fluctuations in subcellular organelles and the zebrafish digestive tract

The precise regulation of pH in biological systems, including intracellular organelles and tissues, is essential to the normal functions of vital movement. Accurate pH determination will contribute to a better understanding of related physiological processes and the effective monitoring of physiologic derangements. Luminescence imaging and sensing are useful tools for biological study. However, the conventional intensity-based detection method suffers from low signal-to-noise ratio. Herein, we report a water-soluble ratiometric phosphorescent probe (P-pH) for measuring pH fluctuations in biological samples based on ratiometric photoluminescence imaging and photoluminescence lifetime imaging. P-pH consists of a pH-responsive iridium(iii) complex, pH-inert iridium(iii) complex, and hydrophilic poly(N-vinyl-2-pyrrolidone). Owing to its dual emission, P-pH was successfully used to monitor the pH variation in mitochondria and lysosomes based on the ratiometric readout. Using P-pH, the reliable evaluation of three types of pH modifiers in the zebrafish digestive tract was also realized with a distinguishable long emission lifetime. This is the first example of assessing pH modifiers in real animal models using a luminescent approach.

A near-infrared phosphorescent probe for F- based on a cationic iridium(III) complex with triarylboron moieties

In this work, a near-infrared (NIR) phosphorescent probe for F- based on a cationic Ir(III) complex [Ir(Bpq)2(quqo)]PF6 (1) with dimesitylboryl (Mes2B) groups on the cyclometalated CN ligands (Bpq) and 2-(quinolin-2-yl)qui

Cationic iridium(III) complex containing both triarylboron and carbazole moieties as a ratiometric fluoride probe that utilizes a switchable triplet-singlet emission

A novel cationic IrIII complex [Ir(Bpq)2(CzbpyCz)] PF6 (Bpq = 2-[4-(dimesitylboryl)phenyl]quinoline, CzbpyCz = 5,5′-bis(9-hexyl-9H-carbazol-3-yl) -2,2′ -bipyridine) containing both triarylboron and carbazole moieties was synthesized. The excited-state properties of [Ir(Bpq)2(CzbpyCz)]PF6 were investigated through UV/Vis absorption and photoluminescence spectroscopy and molecular-orbital calculations. This complex displayed highly efficient orange-red phosphorescent emission with an emission peak of 583 nm and quantum efficiency of φ = 0.30 in dichloromethane at room temperature. The binding of fluoride ions to [Ir(Bpq)2(CzbpyCz)]PF6 can quench the phosphorescent emission from the IrIII complex and enhance the fluorescent emission from the NN ligand, which corresponds to a visual change in the emission from orange-red to blue. Thus, both colorimetric and ratiometric fluoride sensing can be realized. Interestingly, an unusual intense absorption band in the visible region was observed. And the detection of F- ions can also be carried out with visible light as the excitation wavelength. More importantly, the linear response of the probe absorbance change at λ= 351 nm versus the concentration of F- ions allows efficient and accurate quantification of F- ions in the range 0-50 μM.

Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach

Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.

Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.

Ruthenium complex and preparation method thereof and catalytic application

The invention discloses a ruthenium complex and a preparation method thereof and catalytic application. The ruthenium complex is reported for the first time. Research finds that the ruthenium complexhas the activity of catalytically synthesizing quinazoline and derivatives thereof or catalytically synthesizing quinoline and derivatives thereof. When the ruthenium complex provided by the inventionis used for catalytic synthesis of quinazoline and derivatives thereof or quinoline and derivatives thereof, the ruthenium complex has the advantages of mild reaction conditions, wide substrate range, high catalytic product yield and good functional group tolerance, and is significantly superior to the prior art.

A cobalt-catalyzed method for synthesizing quinoline and quinazoline compounds

The present invention discloses a cobalt-catalyzed synthesis of quinoline and quinazoline compounds, by a benzene compound with amino and hydroxyl groups or benzonitrile compounds as raw materials, in the presence of a catalyst and a base by a receptor-fr

Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt

A ruthenium complex bearing a functional 2,2′-bibenzimidazole ligand [(p-cymene)Ru(BiBzImH2)Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically active molecular was also undertaken. Notably, this research exhibits new potential of metal–ligand bifuctional catalysts for acceptorless dehydrogenative reactions.

The preparation of a Co@C3N4catalyst and applications in the synthesis of quinolines from 2-aminobenzyl alcohols with ketones

An unsymmetrical diphenylphosphino-pyridinyl-triazole ligand was synthesized and characterized through IR, NMR and MS and the corresponding earth-abundant metal complex (cobalt) was prepared. Considering energy consumption and environmental friendliness, it is necessary to turn this diphenylphosphino-pyridinyl-triazole cobalt complex into a recyclable catalyst, which could easily be reused. Therefore, a heterogeneous catalyst was synthesized through Co-doping of C3N4, and the Co-nanoparticles on C3N4revealed high catalytic activity for the synthesis of quinolines with good recovery performance.