17012-49-6

Basic information

• Product Name: 5,7-Dibromo-8-methoxyquinoline
• Synonyms: 5,7-Dibromo-8-methoxyquinoline
• CAS NO: 17012-49-6
• Molecular Formula: C₁₀H₇Br₂NO
• Molecular Weight: 316.98
• Mol File: 17012-49-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5,7-Dibromo-8-methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-Dibromo-8-methoxyquinoline(17012-49-6)
• EPA Substance Registry System: 5,7-Dibromo-8-methoxyquinoline(17012-49-6)

Safety Data

• Hazardous Substances Data: 17012-49-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5,7-Dibromo-8-methoxyquinoline is used as an intermediate in the synthesis of various pharmaceuticals for its potential therapeutic effects. Its unique structure allows for the development of new drugs with improved efficacy and selectivity.
Used in Cancer Treatment Research:
5,7-Dibromo-8-methoxyquinoline is used as a research compound for studying its antiproliferative properties against cancer cells. Its potential to inhibit the growth and proliferation of cancer cells makes it a valuable candidate for further investigation in oncology.
Used in Antimicrobial Applications:
5,7-Dibromo-8-methoxyquinoline is used as an antimicrobial agent due to its ability to combat microbial infections. Its broad-spectrum activity against various pathogens highlights its potential use in the development of new antimicrobial drugs to address the growing issue of antibiotic resistance.
Used in Medicinal Chemistry Research:
5,7-Dibromo-8-methoxyquinoline is used as a research reagent in medicinal chemistry to explore its potential applications in the treatment of various diseases and disorders. Its unique chemical properties and biological activities provide a foundation for the design and synthesis of novel therapeutic agents.
Used in Organic Synthesis:
5,7-Dibromo-8-methoxyquinoline is used as an intermediate in the synthesis of various organic compounds, leveraging its reactive functional groups for the formation of new chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 938-33-0 8-methoxyquinoline 
• 521-74-4 broxyquinoline 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 170959-64-5 2,2-dimethyl-N-(2-(7-bromo-8-methoxy-5-quinolinyl)phenyl)propanamide 
• 170959-65-6 2,2-dimethyl-N-(2-(7-bromo-8-methoxy-5-quinolinyl)-4-methoxyphenyl)propanamide 
• 170959-58-7 7-bromo-5-phenyl-8-methoxyquinoline 
• 172795-91-4 2,2-dimethyl-N-(2-(8-methoxy-5-phenyl-7-quinolyl)phenyl)propanamide 
• 172795-94-7 7-(2-azidophenyl)-8-methoxy-5-phenylquinoline 
• 172795-92-5 7-(2-aminophenyl)-5-phenyl-8-methoxyquinoline 
• 170959-76-9 5-(2-azido-5-methoxyphenyl)-7-bromo-8-methoxyquinoline 
• 170959-75-8 5-(2-azidophenyl)-7-bromo-8-methoxyquinoline 
• 170959-71-4 5-(2-amino-5-methoxyphenyl)-7-bromo-8-methoxyquinoline 
• 170959-70-3 5-(2-aminophenyl)-7-bromo-8-methoxyquinoline 
• 182816-50-8 (5-Bromo-8-methoxy-quinolin-7-yl)-(2-methoxy-phenyl)-methanone 
• 182816-49-5 (5-Bromo-8-methoxy-quinolin-7-yl)-(2-methoxy-phenyl)-methanol 

Relevant articles and documents

Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core

Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respe

A novel blue emission PLED material: Synthesis, photophysical and electrochemical properties

A novel π-conjugated polymer (PCQH) containing N-benzylcarbazole and 8-methoxyquinoline units has been successfully synthesized and characterized. The polymer possesses good thermal stability with the decomposition temperature (Td) of 295 °C and the glass transition temperature (Tg) of 250 °C. The absorption and emission spectra show that the polymer can emit blue light with higher fluorescence quantum yield (81%) in CHCl3. With the increase of solvent polarity, the emission peaks of PCQH display an obvious red-shifted. The study of the interactions of PCQH with electron donor (DMA) and electron acceptor (DMTP) indicates that the polymer has excellent electron transfer property. Furthermore, the interactions of PCQH with carbon materials (C60 and CNTs) also have been investigated. The electrochemical properties and energy levels of PCQH were calculated by the Gaussian 09 software, which are correspond to the experiment detection with cyclic voltammetry method.

A SAR study: Evaluation of bromo derivatives of 8-substituted quinolines as novel anticancer agents

Background: Brominated 8-hydroxy, 8-methoxy, 8-amino quinolines 5, 6, 8, 9 and novel cyano 8-hydroxyquinolines 11, 12 were evaluated in vitro for their anticancer effects on various cell lines. 5, 7-Dibromo- 5, 7-bromo- 6, 7-cyano- 11 and 5, 7-dicyano-12 8-hydroxyquinolines were shown to have strong antiproliferative activity against various tumor cell lines, including C6 (rat brain tumor), HeLa (human cervix carcinoma), and HT29 (human colon carcinoma) with IC50 values ranged from 6.7 to 25.6 μg/mL. Methods: A structure activity relationship (SAR) was conducted that quinoline core containing hydroxly group at C-8 positon led to more anti cancer potentials. Results: The results of Lactate Dehydrogenase (LDH) cytotoxic, DNA laddering and inhibition assays indicated that 5, 6, 11 and 12 have high cytotoxic effects and appototic potentials. Conclusion: Furthermore, 5 and 12 have inhibitory effects on relaxation of supercoiled plazmid DNA by supressed the Topoisomerase I enzyme. As a result, 5, 6, 11 and 12 may have promising anticancer drug potential and 5 and 12 may be novel topoisomerase inhibitors.

Luminescent Tungsten(VI) Complexes: Photophysics and Applicability to Organic Light-Emitting Diodes and Photocatalysis

The synthesis, excited-state dynamics, and applications of two series of air-stable luminescent tungsten(VI) complexes are described. These tungsten(VI) complexes show phosphorescence in the solid state and in solutions with emission quantum yields up to 22 % in thin film (5 % in mCP) at room temperature. Complex 2 c, containing a 5,7-diphenyl-8-hydroxyquinolinate ligand, displays prompt fluorescence (blue–green) and phosphorescence (red) of comparable intensity, which could be used for ratiometric luminescent sensing. Solution-processed organic light-emitting diodes (OLEDs) based on 1 d showed a stable yellow emission with an external quantum efficiency (EQE) and luminance up to 4.79 % and 1400 cd m?2respectively. These tungsten(VI) complexes were also applied in light-induced aerobic oxidation reactions.

NITROGEN-CONTAINING HETEROARYL COMPOUNDS HAVING HIV INTEGRASE INHIBITORY ACTIVITY

A compound of the formula (I): wherein Z4, Z5 and Z9 each is independently carbon atom or nitrogen atom; Y is hydroxy, mercapto or amino; RA is a group of the formula: (wherein C ring is nitrogen-containing heteroaryl) has an inhibitory activity against integrase.

Synthesis of substituted 8-methoxyquinolines by regioselective bromine-lithium exchange of 5,7-dihalo-8-methoxyquinolines and 7-bromo-8-methoxyquinoline

Reaction of phenyllithium with 7-bromo-8-methoxyquinoline, 5,7-dibromo-8-methoxyquinoline and 5,7-diiodo-8-methoxyquinoline has been studied. Thus, bromine-lithium exchange of 7-bromo-8-methoxyquinoline gave the 7-lithio-8-methoxyquinoline which reacted with various electrophiles to afford 7-substituted 8-methoxyquinolines 3a-e. The same procedure was also applied to 5,7-dibromo-8-methoxyquinoline, which because of the high regioselectivity of the reaction, led to 7-substituted 5-bromo-8-methoxyquinolines 4a-f; one of them was used for the preparation of a pyridopyranoquinoline.

A CONVENIENT ACCESS TO FUROQUINOLINES AND TO FUROPYRIDINES VIA SRN1 REACTIONS

The two steps route to furoquinolines 4 or to furopyridines 17 involves an SRN1 reaction between 5-chloro-7-iodo-8-isopropoxyquinoline 1a or 2-bromo-3-isopropoxypyridine 15 and enolates derived from ketones.The substitution produc