16567-18-3

Usage

Uses

Used in Organic Synthesis:
8-Bromoquinoline is used as a key intermediate in the synthesis of various organic compounds, including:
1. 8-(Dimesitylboryl)quinolone (ambiphilic molecule) for the development of new materials and applications in organic chemistry.
2. 5H-Pyrido[3,2,1-ij]quinolin-3-one, via palladium-catalyzed coupling reaction with acrolein, for the creation of novel heterocyclic compounds with potential applications in pharmaceuticals and materials science.
3. 8-(1-Hydroxyethyl)quinolone, which can be utilized in the synthesis of pharmaceuticals and other organic compounds.
4. 8-Quinolylcyclopentadienyl metal complexes, via reaction with zincated cyclopentadienyl derivatives of Fe, Mn, and Re in the presence of bis(triphenylphosphine)palladium(0), for the development of new organometallic compounds with potential applications in catalysis and materials science.
5. N,N′-Biquinolines by a coupling reaction using tris(triphenylphosphine)nickel(0) and a zerovalent pyridine-nickel complex, which can be used in the synthesis of complex organic molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
8-Bromoquinoline is used as a building block for the synthesis of pharmaceutical reagents, contributing to the development of new drugs and therapeutic agents.
Used in Dye and Pigment Industry:
8-Bromoquinoline is used as a precursor in the synthesis of dyes and pigments, enabling the production of a wide range of colorants for various applications, including textiles, plastics, and printing inks.
Used in Food Industry:
8-Bromoquinoline is used in the synthesis of food colors, providing a variety of color options for the food and beverage industry.
Used in Analytical Chemistry:
8-Bromoquinoline is used as a pH indicator, playing a crucial role in the measurement and control of pH levels in various chemical and biological processes.

InChI:InChI=1/C9H6BrN/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H

Upstream product

• 56-81-5 glycerol 
• 615-36-1 2-bromoaniline 
• 91-22-5 quinoline 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 55936-96-4 1,2,3,4-tetrahydro-quinoline-8-sulfonic acid 
• 7732-18-5 water 
• 578-66-5 8-amino quinoline 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 936-71-0 2-bromo-N-(prop-2-ynyl)aniline 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 86-58-8 8-quinolinylboronic acid 
• 937640-02-3 8-bromo-1,2,3,4-tetrahydroquinoline 

Downstream Products

• 91-22-5 quinoline 
• 86-58-8 8-quinolinylboronic acid 
• 139366-35-1 8-bromo-5-nitroquinoline 
• 73048-42-7 8-(2-Hydroxyethyl)quinoline 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 308110-36-3 N,N-diethyl-4-[hydroxy(8-quinolinyl)methyl]benzamide 
• 784-84-9 phenyl(quinolin-8-yl)amine 
• 133330-95-7 N-(1-Phenethyl-piperidin-4-yl)-N-quinolin-8-yl-acetamide 
• 133330-88-8 N-(1-Phenethyl-piperidin-4-yl)-N-quinolin-8-yl-propionamide 
• 845830-51-5 N-[(1R)-1-(2-fluoro-4-quinolin-8-ylphenyl)ethyl]-1-[(trifluoroacetyl)-amino]cyclopropanecarboxamide 
• 866082-48-6 C₂₂H₂₃NO₅ 
• 380359-19-3 4-(quinolin-8-yl)benzaldehyde 

Relevant academic research and scientific papers

Electrochemical and spectroscopic behaviors of a novel ruthenium(II) Complex with a Six-Membered Chelate Structure

A novel polypyridyl ruthenium(II) complex with a six-membered chelate ring ([Ru(dmb)2(8pyq)]2+) was designed and synthesized. The oxidation potential was shifted to the negative potential direction, and relatively intense metal-to-ligand charge transfer absorption in the longer-wavelength region was observed for [Ru(dmb)2(8pyq)]2+ compared with the reference complexes without any six-membered chelate rings. The electrochemical and spectroscopic properties of [Ru(dmb)2(8pyq)]2+ were discussed in terms of the chelate structure and coordination geometry with utilization of theoretical calculations.

Kinetic Resolution of Axially Chiral 5- or 8-Substituted Quinolines via Asymmetric Transfer Hydrogenation

An efficient kinetic resolution of axially chiral 5- or 8-substituted quinoline derivatives was developed through asymmetric transfer hydrogenation of heteroaromatic moiety, simultaneously obtaining two kinds of axially chiral skeletons with up to 209 of selectivity factor. This represents the first successful application of asymmetric transfer hydrogenation of heteroaromatics in kinetic resolution of axially chiral biaryls.

Optical p Ka Control in a Bifunctional Iridium Complex

There are few ways to switch a catalyst's reactivity on or off, or change its selectivity, with external radiation; many of these involve photochemical activation of a catalyst. In the case of homogeneous late-transition-metal catalysts, the metal complex itself is frequently the chromophore involved in such reactivity switching. We show here a base-pendant ligand-metal bifunctional scaffold wherein a photobase, a compound that becomes more basic in the excited state (pKa a?), is used to switch the proton acceptor ability on an active site of the complex. The system differs from those with metal-centered chromophores, because the photobase operates independently of the metal. While excellent progress has been made in photoacid chemistry, neither a photoacid nor a photobase has been designed into the structure of a transition-metal catalyst where the metal is not part of the chromophore. We find that quinoline is an efficient photobase that preserves its unique properties in the close proximity of an iridium center: the efficacy of the photobase (9.3 a? a control in a transition-metal complex.

Synthesis of functionalized porphyrins as oxygen ligand receptors

Oxophilic synthetic receptors were designed and synthesized using a porphyrin scaffold, with the aim of constructing a preorganized complementary binding site for phenols and carbohydrates. We pursued three strategies for phenol recognition: (1) Lewis aci

Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group

Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functiona

Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents

Microtubule-targeting agents (MTAs) are a class of clinically successful anti-cancer drugs. The emergence of multidrug resistance to MTAs imposes the need for developing new MTAs endowed with diverse mechanistic properties. Benzoxazepines were recently identified as a novel class of MTAs. These anticancer agents were thoroughly characterized for their antitumor activity, although, their exact mechanism of action remained elusive. Combining chemical, biochemical, cellular, bioinformatics and structural efforts we developed improved pyrrolonaphthoxazepines antitumor agents and their mode of action at the molecular level was elucidated. Compound 6j, one of the most potent analogues, was confirmed by X-ray as a colchicine-site MTA. A comprehensive structural investigation was performed for a complete elucidation of the structure-activity relationships. Selected pyrrolonaphthoxazepines were evaluated for their effects on cell cycle, apoptosis and differentiation in a variety of cancer cells, including multidrug resistant cell lines. Our results define compound 6j as a potentially useful optimized hit for the development of effective compounds for treating drug-resistant tumors.

Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation

A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time.

Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts

The enantioselective syntheses of axially chiral heterobiaryls were accomplished through the aromatic electrophilic halogenation of 3-(quinolin-8-yl)phenols with bifunctional organocatalysts that control the molecular conformations during successive halogenations. Axially chiral quinoline derivatives, which have rarely been synthesized in an enantioselective catalytic manner, were afforded in moderate-to-good enantioselectivities through bromination, and an analogous protocol also enabled enantioselective iodination. In addition, this catalytic reaction, which allows enantioselective control through the use of mono-ortho-substituted substrates, allowed the asymmetric synthesis of 8-arylquinoline derivatives bearing two different halogen groups in high enantioselectivities.

Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions

The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.