580-18-7

Basic information

• Product Name: 3-Hydroxyquinoline
• Synonyms: 3-HYDROXYQUINOLINE;3-QUINOLOL;quinolin-3-ol;3-HYDROXYQUINOLINE 98%;3-HYDROXYQUINOLINE, 97+%;3-Quinolinol;3-Hydroxyquinoline, 95+%;CCRIS 4328
• CAS NO: 580-18-7
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 209-456-7
• Product Categories: Heterocyclic Series
• Mol File: 580-18-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 198-202°C
• Boiling Point: 264.27°C (rough estimate)
• Flash Point: 143.1oC
• Appearance: Beige/Crystalline Powder
• Density: 1.1555 (rough estimate)
• Vapor Pressure: 0.000278mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.28(at 20℃)
• Water Solubility: 587.9mg/L(20 oC)
• CAS DataBase Reference: 3-Hydroxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxyquinoline(580-18-7)
• EPA Substance Registry System: 3-Hydroxyquinoline(580-18-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RTECS: VC4050000
• Hazardous Substances Data: 580-18-7(Hazardous Substances Data)

Usage

Description

3-Hydroxyquinoline is an organic compound belonging to the quinoline family, characterized by its beige crystalline powder appearance. It is a derivative of quinoline that has undergone metabolism by cytochrome P450, which is an essential enzyme in the metabolism of various substances in the body.

Uses

Used in Pharmaceutical Industry:
3-Hydroxyquinoline is used as a chemical reagent for the preparation of cyclic peptides with antitumor functionality. Its role in the pharmaceutical industry is crucial, as it aids in the development of potential cancer-fighting agents.
Used in Metabolic Studies:
As a quinoline derivative resulting from the metabolism by cytochrome P450, 3-Hydroxyquinoline is also utilized in research and studies related to metabolic processes. This application helps in understanding the role of cytochrome P450 in the metabolism of various substances and its implications on human health.

InChI:InChI=1/C9H7NO/c11-8-5-7-3-1-2-4-9(7)10-6-8/h1-6,11H

Upstream product

• 580-17-6 3-aminoquinoline 
• 118-13-8 3-hydroxyquinoline-4-carboxylic acid 
• 91-22-5 quinoline 
• 32888-92-9 quinolin-3-yl benzoate 
• 5332-24-1 3-bromoquinoline 
• 141-46-8 Glycolaldehyde 
• 529-23-7 o-aminobenzaldehyde 
• 13669-42-6 3-quinolylcarboxaldehyde 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 191162-39-7 quinolin-3-ylboronic acid 
• 7732-18-5 water 
• 50-81-7 ascorbic acid 
• 7758-99-8 copper(II) sulfate 
• 486-74-8 4-quinolinic acid 

Downstream Products

• 112991-88-5 orthoformic acid-[3]quinolyl ester-diphenyl ester 
• 32888-92-9 quinolin-3-yl benzoate 
• 92856-20-7 toluene-4-sulfonic acid quinolin-3-yl ester 
• 3418-45-9 1,2,3,4-tetrahydroquinolin-3-ol 
• 315228-25-2 3-chloro-5-fluoro-4-(quinolin-3-yloxy)nitrobenzene 
• 6480-68-8 quinoline-3-carboxylic acid 
• 32435-61-3 4-bromo-3-hydroxyquinoline 

Relevant articles and documents

Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols

A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.

Convenient synthesis of 3-Hydroxyquinolines via dakin oxidation: A short synthesis of Jineol

A convenient synthesis of 3-hydroxyquinolines has been described via unprecedented Dakin oxidation of quinoline-3-carboxaldehydes. Subsequently, application of the methodology to a high yielding synthesis of quinoline alkaloid Jineol (1) is reported.

Palladium-Catalyzed Hydroxylation of Aryl Halides with Boric Acid

Boric acid, B(OH)3, is proved to be an efficient hydroxide reagent in converting (hetero)aryl halides to the corresponding phenols with a Pd catalyst under mild conditions. Various phenol products were obtained in good to excellent yields. This transformation tolerates a broad range of functional groups and molecules, including base-sensitive substituents and complicated pharmaceutical (hetero)aryl halide molecules.