1198-14-7

Basic information

• Product Name: 5-bromoquinolin-8-ol
• Synonyms: 5-Bromo-8-quinolinol;5-BROMO-8-HYDROXY QUINOLINE;5-Bromoquinolin-8-ol;8-Quinolinol, 5-broMo- 5-BroMo-8-hydroxyquinoline;5-BroMo-8-hydroxyquinoline, 96.0%(GC);5-Bromo-8-oxyquinoline;8-Quinolinol, 5-bromo-
• CAS NO: 1198-14-7
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• EINECS: 214-829-2
• Product Categories: Haloquinolines;Hydroxyquinolines;Quinolines;Phenylamine Series
• Mol File: 1198-14-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 127 °C
• Boiling Point: 362.7 °C at 760 mmHg
• Flash Point: 173.2 °C
• Appearance: /
• Density: 1.5708 (rough estimate)
• Vapor Pressure: 9.07E-06mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 3.77±0.10(Predicted)
• CAS DataBase Reference: 5-bromoquinolin-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromoquinolin-8-ol(1198-14-7)
• EPA Substance Registry System: 5-bromoquinolin-8-ol(1198-14-7)

Safety Data

• RTECS: VC4582000
• Hazardous Substances Data: 1198-14-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Bromoquinolin-8-ol is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and pharmaceutical products. Its unique structural features make it a valuable building block in the production of various organic molecules.
Used in Agrochemical Production:
In the agrochemical industry, 5-bromoquinolin-8-ol is utilized as a starting material for the synthesis of various agrochemicals, contributing to the development of effective and innovative products for agricultural applications.
Used in Medicinal Chemistry Research:
5-Bromoquinolin-8-ol is employed as a research compound in medicinal chemistry, where its biological activities and structural properties are studied to explore its potential in drug discovery and the development of novel therapeutic agents.
Used in Drug Discovery:
As a compound with potential applications in medicinal chemistry, 5-bromoquinolin-8-ol is used in drug discovery processes to identify and develop new pharmaceuticals with improved efficacy and safety profiles. Its unique structural features make it a promising candidate for the development of innovative drug candidates.

InChI:InChI=1/C9H6BrNO/c10-7-3-4-8(12)9-6(7)2-1-5-11-9/h1-5,12H

Upstream product

• 148-24-3 8-quinolinol 
• 40925-68-6 2-amino-4-bromo-phenol 
• 56-81-5 glycerol 
• 13207-66-4 5-amino-8-hydroxyquinoline 

Downstream Products

• 37171-61-2 5-bromo-7-iodo-quinolin-8-ol 
• 236753-48-3 5-(N-phenylanilino)quinolin-8-ol 

Relevant articles and documents

Visible light-induced mono-bromination of arenes with BrCCl3

A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.

Hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, preparation method and applications thereof

The invention discloses a hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups, a preparation method and applications thereof.According to the invention, the hydroxyquinolinyl metal organic small molecule cooperation compound material grafted with perylene diimide and aromatic groups is obtained through a Stille coupling reaction and a metal coordination reaction; the metal organic small molecule cooperation compound belongs to branched small molecules, the structure of the metal organic small molecule cooperation compound uses a metal as a core, and a branched chain contains hydroxyquinoline and a perylene diimide and electron-donating aromatic group unit; hydroxyquinoline has high electron withdrawing capacity, the grafted perylene diimide unit is beneficial to improving the crystallization capacity and the electron affinity of small molecules, the electron donating capacity is enhanced by linking the electrondonating aromatic group to the perylene diimide unit, and the push-pull electron effect is easily formed with the hydroxyquinoline; and the structure small molecule and the polymer donor form energylevel matching, so that the structure small molecule is suitable for being used as a small molecule acceptor material.

Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes

Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.

A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines

An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.

Chemo-and regioselective bromination of aromatic compounds in the presence of γ-picolinium bromochromate (γ-PBC)/CH3CN

Regioselective oxidative bromination of activated aromatic compounds has been studied using γ-Picolinium bromochromate in either CH3COOH or CH3CN is reported. The results obtained revealed excellent yields of monobromo compounds at para-position under thermal condition especially in methyl cyanide.

Mild, efficient, and regioselective monobromination of arylamines and phenols using [BBIm]Br3 as a new reagent

We report here an efficient method for the synthesis and characterization of the room-temperature ionic liquid 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3) (2) and its application as an efficient reagent and solvent for regioselective bromination of arylamines and phenols under mild conditions. The bromination was carried out in the absence of organic solvents, and in most cases, the only extraction solvent needed was water. The spent 1,3-di-n-butylimidazolium bromide (1) was easily recycled.

A new method of bromination of aromatic rings by an iso-amyl nitrite/HBr system

A mixture of iso-amyl nitrite/HBr is shown to be a mild and efficient reagent for electrophilic aromatic bromination. The reaction succeeds with slightly activated arenes and heterocyclic compounds. By using HCl instead of HBr, chlorination can also be performed in few cases. The i-amONO2/HBr mixture can also be utilized for bromination in the α-position of electron withdrawing groups. A possible mechanism is briefly discussed.