16567-18-3

Basic information

• Product Name: 8-Bromoquinoline
• Synonyms: RARECHEM AK ML 0146;8-BROMOQUINOLINE;8-BROMOQUIOLINE;http://www.ruiyitech.com/detail.phpCAS=578-66-5&class_id=4;8-bromooquinoline;8-Bromoquinoline ,97%;8-Bromoquinoline,96%;Quinoline, 8-Bromo-
• CAS NO: 16567-18-3
• Molecular Formula: C₉H₆BrN
• Molecular Weight: 208.05
• EINECS: -0
• Product Categories: blocks;Bromides;Heterocycles;Quinoline series;Quinolines, Quinazolines and derivatives;Halides;Quinolines, Isoquinolines & Quinoxalines;Quinoline&Isoquinoline;Quinoline Derivertives;Halogenated;Organohalides;Quinoline;Quinolines, Isoquinolines & Quinoxalines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks
• Mol File: 16567-18-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 58-59 °C
• Boiling Point: 112-113 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to yellow-brown/Liquid After Melting
• Density: 1.594 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: n20/D 1.672(lit.)
• Storage Temp.: Refrigerator (+4°C)
• PKA: 2.33±0.17(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 8-Bromoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Bromoquinoline(16567-18-3)
• EPA Substance Registry System: 8-Bromoquinoline(16567-18-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 16567-18-3(Hazardous Substances Data)

Usage

Description

8-Bromoquinoline is a quinolone derivative characterized by the presence of a pyridyl group. It is a white to light yellow crystal powder that is widely used in the synthesis of dyes, food colors, pharmaceutical reagents, pH indicators, and various industrial processes. Its chemical properties allow it to undergo direct heteroarylation reactions with various heteroaromatic compounds in the presence of a palladium catalyst, leading to the formation of polyheteroaromatic derivatives.

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

• 91-22-5 quinoline 
• 7664-93-9 sulfuric acid 
• 7726-95-6 bromine 
• 615-36-1 2-bromoaniline 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 936-71-0 2-bromo-N-(prop-2-ynyl)aniline 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 578-66-5 8-amino quinoline 
• 55936-96-4 1,2,3,4-tetrahydro-quinoline-8-sulfonic acid 
• 7732-18-5 water 
• 56-81-5 glycerol 
• 86-58-8 8-quinolinylboronic acid 
• 1613-37-2 Quinoline N-oxide 
• 90279-39-3 8-bromoquinoline N-oxide 

Downstream Products

• 73048-42-7 8-(2-Hydroxyethyl)quinoline 
• 86-58-8 8-quinolinylboronic acid 
• 491-33-8 8-mercaptoquinoline 
• 406234-25-1 methyl 4-(6-methoxypyridin-3-yl)benzoate 
• 406234-48-8 methyl 4-(quinolin-8-yl)benzoate 
• 91-22-5 quinoline 
• 916314-52-8 5H-pyrido[3,2,1-ij]quinolin-3-one 
• 545445-49-6 3-quinolin-8-yl-propenal 
• 1101859-08-8 C₂₁H₂₂N₂O 
• 1238358-95-6 bis(8-quinolyl)phenylsilane 
• 1260019-77-9 mesityl(quinolin-8-yl)borinic acid 

Relevant articles and documents

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.

Facile Synthesis of 8-Substituted Quinolines

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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

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.