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

Chemical Properties

white to light yellow crystal powder

Uses

8-Bromoquinoline may be used in the following studies:Synthesis of 8-(dimesitylboryl)quinolone (ambiphilic molecule).Direct synthesis of 5H-pyrido[3,2,1-ij]quinolin-3-one, via palladium catalyzed coupling reaction with acrolein.Preparation of 8-(1-hydroxyethyl)quinolone.Preparation of 8-quinolylcyclopentadienyl metal complexes, via reaction with zincated cyclopentadienyl derivatives of Fe, Mn and Re in the presence of bis(triphenylphosphine)palladium(0).Synthesis of n,n′-biquinolines by a coupling reaction using tris(triphenylphosphine)nickel(0) and a zerovalent pyridine-nickel complex.

General Description

8-Bromoquinoline is a quinolone derivative. It is widely employed for the synthesis of dyes, food colors, pharmaceutical reagents, pH indicators and in various industrial processes. Its molecule bears a pyridyl group. It undergoes direct heteroarylation reaction with various heteroaromatic compounds in the presence of a palladium catalyst to afford polyheteroaromatic derivatives.

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 
• 7726-95-6 bromine 
• 578-66-5 8-amino quinoline 
• 91-22-5 quinoline 
• 86-58-8 8-quinolinylboronic acid 
• 1613-37-2 Quinoline N-oxide 
• 90279-39-3 8-bromoquinoline N-oxide 
• 937640-02-3 8-bromo-1,2,3,4-tetrahydroquinoline 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 127-68-4 sodium 3-nitrobenzenesulfonate 
• 936-71-0 2-bromo-N-(prop-2-ynyl)aniline 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 55936-96-4 1,2,3,4-tetrahydro-quinoline-8-sulfonic acid 

Downstream Products

• 91-22-5 quinoline 
• 86-58-8 8-quinolinylboronic acid 
• 139366-35-1 8-bromo-5-nitroquinoline 
• 784-84-9 phenyl(quinolin-8-yl)amine 
• 866082-48-6 C₂₂H₂₃NO₅ 
• 491-33-8 8-mercaptoquinoline 
• 406234-25-1 methyl 4-(6-methoxypyridin-3-yl)benzoate 
• 406234-48-8 methyl 4-(quinolin-8-yl)benzoate 
• 916314-52-8 5H-pyrido[3,2,1-ij]quinolin-3-one 
• 545445-49-6 3-quinolin-8-yl-propenal 
• 1101859-08-8 C₂₁H₂₂N₂O 
• 1223575-57-2 N-2,6-diethylphenyl-quinolinyl-8-amine 
• 1223575-58-3 N-2,6-diisopropylphenyl-quinolinyl-8-amine 
• 1223575-55-0 N-2,6-dimethylphenyl-quinolinyl-8-amine 

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.