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

• 103914-52-9 2-(4'-bromophenyl)quinoline-4-carboxylic acid 
• 5344-90-1 2-Aminobenzyl alcohol 
• 99-90-1 para-bromoacetophenone 
• 5391-88-8 1-(4-bromophenyl)ethanol 
• 612-62-4 2-Chloroquinoline 
• 5467-74-3 4-Bromophenylboronic acid 
• 181867-44-7 C₁₅H₁₀BrNO₃ 
• 1613-37-2 Quinoline N-oxide 
• 2297-64-5 p-bromophenylsulfonyl hydrazide 
• 91-22-5 quinoline 
• 529-23-7 o-aminobenzaldehyde 
• 91-56-5 indole-2,3-dione 
• 552-89-6 2-nitro-benzaldehyde 
• 99-73-0 para-bromophenacyl bromide 

Downstream Products

• 132318-11-7 4-[2]quinolyl-benzoic acid 
• 1016275-42-5 (S)-2-(4-bromophenyl)-1,2,3,4-tetrahydroquinoline 
• 1312162-99-4 (R)-2-(4-bromophenyl)-1,2,3,4-tetrahydroquinoline 
• 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 

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.

NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines

Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.

Quinoline derivative as well as preparation method and application thereof

The invention belongs to the technical field of chemical drug synthesis, and particularly relates to a quinoline derivative as well as a preparation method and application thereof. In a reaction system, firstly, a metal catalyst, a ligand and a silicon hydrogen reagent interact to generate metal hydride, the metal hydride and an alkyne compound are subjected to addition, the metal hydride and an anthranil compound are subjected to an electrophilic amination reaction, and then the polysubstituted quinoline derivative is obtained through intramolecular cyclization. According to the invention, the starting raw materials such as the alkyne and the anthranil compound of the reaction are cheap and easily available, a variety of different polysubstituted quinoline derivatives can be constructed by using the one-step method, and can be rapidly converted into other compounds through the oxidation, the reduction, the coupling and other approaches of the target molecule so as to provide the good application prospect in the fields of drug development and material preparation; and the method is mild in condition, green, efficient, simple to operate and very suitable for large-scale industrial production.

Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines

A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.

Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes

The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.

Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.

Bioinspired Radical-Mediated Transition-Metal-Free Synthesis of N-Heterocycles under Visible Light

A redox-active iminoquinone motif connected with π-delocalized pyrene core has been reported that can perform efficient two-electron oxidation of a class of substrates. The design of the molecule was inspired by the organic redox cofactor topaquinone (TPQ), which executes amine oxidation in the enzyme, copper amine oxidase. Easy oxidation of both primary and secondary alcohols happened in the presence of catalytic KOtBu, which could reduce the ligand backbone to its iminosemiquinonate form under photoinduced conditions. Moreover, this easy oxidation of alcohols under aerobic condition could be elegantly extended to multi-component, one-pot coupling for the synthesis of quinoline and pyrimidine. This organocatalytic approach is very mild (70 °C, 8 h) compared to a multitude of transition-metal catalysts that have been used to prepare these heterocycles. A detailed mechanistic study proves the intermediacy of the iminosemiquinonate-type radical and a critical hydrogen atom transfer step to be involved in the dehydrogenation reaction.