938-33-0

Usage

Uses

8-Methoxyquinoline is used as pharmaceutical intermediate.

InChI:InChI=1/C10H9NO/c1-12-9-6-2-4-8-5-3-7-11-10(8)9/h2-7H,1H3

Upstream product

• 70945-35-6 5-amino-8-methoxyquinoline 
• 90-04-0 2-methoxy-phenylamine 
• 56-81-5 glycerol 
• 93-26-5 2-methoxyacetanilide 
• 148-24-3 8-quinolinol 
• 75-09-2 dichloromethane 
• 80-18-2 Methyl benzenesulfonate 
• 74-88-4 methyl iodide 
• 36748-99-9 7-bromo-8-(methyloxy)quinoline 
• 17012-50-9 5,7-diiodo-8-methoxyquinoline 
• 1416801-74-5 8-methoxy-3-iodoquinoline 
• 67-56-1 methanol 
• 611-33-6 8-chloroquinoline 
• 53899-17-5 8-methoxy-1,2,3,4-tetrahydroquinoline 

Downstream Products

• 97554-55-7 8-methoxy-1-(3-trimethylammonio-propyl)-quinolinium; dibromide 
• 855625-62-6 (8-methoxy-[5]quinolyl)-(4-nitro-phenyl)-ketone 
• 393109-89-2 8-methoxy-2-phenylquinoline 
• 148-24-3 8-quinolinol 
• 17012-47-4 8-methoxy-5-nitroquinoline 
• 71083-22-2 8-Methoxy-3-ethoxycarbonyl-chinolin 
• 73459-98-0 ethyl 8-methoxyquinoline-4-carboxylate 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 
• 53899-17-5 8-methoxy-1,2,3,4-tetrahydroquinoline 
• 75414-07-2 8-methoxy-5,6,7,8-tetrahydroquinoline 
• 89847-82-5 2-(8-methoxy-[2]quinolyl)-phenol 
• 676255-10-0 8-hydroxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester 
• 6640-50-2 1,2,3,4-tetrahydroquinolin-8-ol 
• 14631-46-0 5,6,7,8-tetrahydroquinoline-8-ol 

Relevant academic research and scientific papers

Quinoline-based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors

A series of substituted quinolines was screened for their antiproliferative, cytotoxic, antibacterial activities, DNA/protein binding affinity, and anticholinergic properties by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide cell proliferation, lactate dehydrogenase cytotoxicity, and microdilution assays, the Wolfe–Shimmer equality method, the Ellman method, and the esterase assay, respectively. The results of the cytotoxic and anticancer activities of the compounds displayed that 6-bromotetrahydroquinoline (2), 6,8-dibromotetrahydroquinoline (3), 8-bromo-6-cyanoquinoline (10), 5-bromo-6,8-dimethoxyquinoline (12), the novel N-nitrated 6,8-dimethoxyquinoline (13), and 5,7-dibromo-8-hydroxyquinoline (17) showed a significant antiproliferative potency against the A549, HeLa, HT29, Hep3B, and MCF7 cancer cell lines (IC50 = 2–50 μg/ml) and low cytotoxicity (～7–35percent) as the controls, 5-fluorouracil and cisplatin. The compound–DNA linkages are hyperchromic or hypochromic, causing variations in their spectra. This situation shows that they can be bound to DNA with the groove-binding mode, with Kb value in the range of 2.0 × 103–2.2 × 105 M–1. Studies on human Gram(+) and Gram(?) pathogenic bacteria showed that the substituted quinolines exhibited selective antimicrobial activities with MIC values of 62.50–250 μg/ml. All tested quinoline derivatives were found to be effective inhibitors of acetylcholinesterase (AChE) and the human carbonic anhydrase I and II isoforms (hCA I and II), with Ki values of 46.04–956.82 nM for hCA I, 54.95–976.93 nM for hCA II, and 5.51–155.22 nM for AChE. As a result, the preliminary data showed that substituted quinolines displayed effective pharmacological features. Molecular docking studies were performed to investigate the binding modes and interaction energies for compounds 2–17 with AChE (PDB ID: 4EY6), hCA I (PDB ID: 1BMZ), and hCA II (PDB ID: 2ABE).

Development of highly selective dual mode chromogenic and fluorogenic chemosensor for Bi3+ ions

A new dual mode chemosensor 8-methoxy-2-(thiophen-2-yl) quinolone (L) was synthesised for selective and sensitive detection of Bi3+ ions. The selective distinct colorimetric response and fluorescence quenching were observed upon interaction of L with Bi3+ in CH3CN:H2O (85:15, v/v) media. The sensor L could form 2:1 stoichiometric complex with Bi3+ with an association constant of 2.2 × 105 M?2 by using Benesi-Hilderbrand (BH) method. The fluorescence quenching constant estimated to be 9.3 × 108 M?1 by using Stern-Volmer (SV) plot. The lowest detection limit of Bi3+ by colorimetric and fluorimetric were found to be 1.78 μM and 0.057 μM respectively. The sensing mechanism of L with Bi3+ was studied using 1H NMR, ESI-mass analysis and theoretical calculations. Finally, the sensor L was applied for the detection of Bi3+ in various water and pharmaceutical drug samples.

A simple unimolecular multiplexer/demultiplexer

Simple but effective! 8-Methoxyquinoline, an unsophisticated fluorophore, displays both 2:1 multiplexer and 1:2 demultiplexer digital functions (see picture). Protonation of the fluorophore results in completely different optical spectral profiles and multiplexing/demultiplexing behavior is obtained by exploiting the proton-driven reversible modulation of two complementary absorption and fluorescence signals. (Figure Presented).

Iridium-Catalyzed Site-Selective Borylation of 8-Arylquinolines

We report a convenient method for the highly site-selective borylation of 8-arylquinoline. The reaction proceeds smoothly in the presence of a catalytic amount of [Ir(OMe)(cod)] 2and 2-phenylpyridine derived ligand using bis(pinacolato)diborane as the borylating agent. The reactions occur with high selectivity with many functional groups, providing a series of borylated 8-aryl quinolines with good to excellent yield and excellent selectivity. The borylated compounds formed in this method can be transformed into various important synthons by using known transformations.

Tetradentate cyclometallatin (II) and palladium (II) complex luminescent material containing quinoline structural unit and application thereof

The invention relates to the technical field of organic luminescent materials, and provides a metal platinum (II) and a palladium (II) complex luminescent material containing a quinoline structural unit, as shown below. Compared with the bidentate ligand platinum complex, the cyclometallatin (II) and the palladium (II) complex molecule based on the tetradentate ligand provided by the invention have strong rigidity, can effectively inhibit non-radiative transition caused by molecule vibration, greatly improve the quantum efficiency, and have wide application prospects in the fields OLED display, illumination and the like.

Palladium catalyzed hydrodefluorination of fluoro-(hetero)arenes

Palladium catalyzed hydrodefluorination was developed for fine-tuning the properties of fluoro-(hetero)aromatic compounds. The robust reaction can be set up in air, requires only commercially available components, and tolerates a variety of heterocycles and functionalities relevant to drug discovery. Given the prevalence of fluorine incorporation around metabolic hotspots, the corresponding deuterodefluorination reaction may prove useful for converting fluorinated libraries to deuterated analogues to suppress the oxidative metabolism by kinetic isotope effects.

Corrigendum: Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles (Chemistry - A European Journal, (2017), 23, 57, (14167-14172), 10.1002/chem.201703642)

The authors have been alerted to an error that was unfortunately missed at the time of publication. Table was duplicated with Table 4. The correct version of Table 2 is shown below. The authors apologise for any inconvenience caused. Organo-photoredox catalyzed oxidative dehydrogenation of tetrahydroquinolines (THQ).[a,b] (Table presented.) [a] Reaction conditions: 1 (0.5 mmol), rose bengal (1.0 mol %), N,N-dimethylacetamide (2.0 mL), open air atmosphere under visible-light irradiation at room temperature for 24 h. [b] Isolated yields. [c] 0.1 mol % of photoredox catalyst for 28 h.

High efficiency microwave-assisted synthesis of quinoline from acrolein diethyl acetal and aniline utilizing Ni/Beta catalyst

A facile and solvent-free microwave-assisted approach to quinoline was developed by utilizing both acrolein diethyl acetal and aniline as reagents, firstly employing Ni/Beta zeolite as mild, ecofriendly and low-cost solid catalyst. As high as 83% yield of quinoline was quickly achieved at a short microwave time. The results indicated that the effect of Ni on Beta zeolite not only significantly promoted conversion of acrolein diethyl acetal to effective intermediate but also dramatically accelerated dehydrogenation rate of tetrahydroquinoline/dihydroquinoline to quinoline.

Experimental and Computational Exploration of para-Selective Silylation with a Hydrogen-Bonded Template

The regioselective conversion of C?H bonds into C?Si bonds is extremely important owing to the natural abundance and non-toxicity of silicon. Classical silylation reactions often suffer from poor functional group compatibility, low atom economy, and insufficient regioselectivity. Herein, we disclose a template-assisted method for the regioselective para silylation of toluene derivatives. A new template was designed, and the origin of selectivity was analyzed experimentally and computationally. An interesting substrate–solvent hydrogen-bonding interaction was observed. Kinetic, spectroscopic, and computational studies shed light on the reaction mechanism. The synthetic significance of this strategy was highlighted by the generation of a precursor of a potential lipophilic bioisostere of γ-aminobutyric acid (GABA), various late-stage diversifications, and by mimicking enzymatic transformations.

Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles

We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.