15450-76-7

Basic information

• Product Name: 2,8-Quinolinediol
• Synonyms: 2,8-DIHYDROXYQUINOLINE;2,8-DIHYDROQUINOLINE;2,8-QUINOLINEDIOL;8-Hydroxycabostyril;8-HYDROXYCARBOSTYRIL;QUINOLINE-2,8-DIOL;2,8-DIHYDROXY-CHINOLIN;2,8-Dihydroxyquinoleine
• CAS NO: 15450-76-7
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: -0
• Product Categories: Quinolines, Quinazolines and derivatives;Quinoline derivatives;Quinoline&Isoquinoline;Quinolines;Heterocycles;Inhibitors
• Mol File: 15450-76-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: ~290 °C (dec.)
• Boiling Point: 403.2 °C at 760 mmHg
• Flash Point: 197.6 °C
• Appearance: white to crystalline powder
• Density: 1.337 g/cm³
• Vapor Pressure: 4.46E-07mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: Room temperature.
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 8.85±0.20(Predicted)
• BRN: 472906
• CAS DataBase Reference: 2,8-Quinolinediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,8-Quinolinediol(15450-76-7)
• EPA Substance Registry System: 2,8-Quinolinediol(15450-76-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 15450-76-7(Hazardous Substances Data)

Usage

Description

2,8-Quinolinediol, also known as 8-hydroxycarbostyril or 8-hydroxyquinolin-2(1H)-one, is a quinolone derivative with a brown powder appearance. It has been identified as a metabolite of 8-hydroxyquinoline-N-oxide in rabbits and has been detected as a new UV-absorbing compound (UAC) in cow milk. The structure of 2,8-Quinolinediol has been elucidated using HRMS and by 1H, 13C, and 1H ×13C NMR techniques.

Uses

Used in Pharmaceutical Compounds:
2,8-Quinolinediol is used as a starting reagent in the preparation of pharmaceutical compounds, particularly due to its quinolone derivative nature.
Used in Toxicity and Pathogenesis Studies:
2,8-Quinolinediol is suitable for use as a standard in studies aimed at identifying urinary metabolites related to toxicity and pathogenesis induced by doxorubicin (DOX) in rats. This application utilizes online and off-line LC-MS techniques to analyze the metabolites.
Used in Asthma Treatment:
2,8-Quinolinediol serves as a starting reagent for the preparation of two potent β2-adrenergic receptor agonists, Procaterol and Indacaterol, which are used for the treatment of asthma. These agonists help in relaxing the smooth muscles of the airways, providing relief from asthma symptoms.
Used in UV-Absorbing Compounds:
As a detected new UV-absorbing compound (UAC) in cow milk, 2,8-Quinolinediol may have potential applications in the development of materials or products that require UV absorption properties, such as sunscreens or protective coatings.

InChI:InChI=1/C9H7NO2/c11-7-3-1-2-6-4-5-8(12)10-9(6)7/h1-5,11H,(H,10,12)

Upstream product

• 148-24-3 8-quinolinol 
• 84-88-8 8-quinolinol-5-sulfonic acid 
• 15450-72-3 2-hydroxyquinolin-8-yl acetate 
• 1127-45-3 8-Hydroxyquinoline-N-oxide 
• 22614-69-3 8-methoxy-1H-quinolin-2-one 
• 77432-37-2 o-(3-ethoxyacryloylamino)phenol 
• 126582-57-8 (E)-N-(2-methoxyphenyl)-3-phenylacrylamide 
• 15450-72-3 2-oxo-1,2-dihydroquinolin-8-yl acetate 
• 90-04-0 2-methoxy-phenylamine 
• 77432-36-1 N-(3-ethoxyacryloyl)-o-anisidine 
• 77432-38-3 N-(3,3-di-n-butoxypropionyl)-o-anisidine 
• 95-55-6 2-amino-phenol 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 
• 39856-08-1 (E)-3,4-dimethoxycinnamic chloride 

Downstream Products

• 15450-72-3 2-hydroxyquinolin-8-yl acetate 
• 22614-69-3 8-methoxy-1H-quinolin-2-one 
• 15450-73-4 2,5,8(1H)-quinolinetrione 
• 193821-72-6 8-(2-Biphenyl-4-yl-2-oxo-ethoxy)-1H-quinolin-2-one 
• 193821-68-0 8-(2-Oxo-2-phenyl-ethoxy)-1H-quinolin-2-one 
• 193821-69-1 8-[2-(4-Fluoro-phenyl)-2-oxo-ethoxy]-1H-quinolin-2-one 
• 193821-73-7 8-[2-(4-Methoxy-phenyl)-2-oxo-ethoxy]-1H-quinolin-2-one 

Relevant articles and documents

Kinetics of procaterol auto-oxidation in buffered acid solutions

The kinetics of procaterol (1) degradaton in buffered acidic solutions (pH 4-6) was investigated using a HPLC procedure. The effect of temperature and ferric ions on the reaction rate was estimated. In acidic solutions, 1 undergoes pseudo first-order degradation with an induction period. The first-order rate constant for degradation increased and the induction period decreased with an increase in pH. Ferric ions catalyzed the degradation reaction and decreased the induction period. At pH 6, the activation energy of the reaction was 34.5 kcal/mol/deg. The results of this study indicate that 1 in solution is more stable at acidic pH, in the absence of heavy metal ions, and protected from air.

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.

Method for preparing hydroxyl-2(1H)-quinolinone

The invention discloses a method for preparing hydroxyl-2(1H)-quinolinone, and belongs to the field of organic chemistry. The method comprises the following steps: enabling an aminophenylboric acid compound and trans-beta-aryl acryloyl chloride to react under the existence of triethylamine or pyridine so as to generate a trans-amide intermediate, and then carrying out temperature rising reaction in an organic solvent under the existence of aluminum chloride anhydrous and B(C6F5)3; cooling after completing the reaction, and adding hydrogen peroxide for oxidization, thus obtaining the hydroxyl-2(1H)-quinolinone. The method disclosed by the invention has the advantages that raw materials are easy to obtain, hydroxyl quinolinone products in different positions can be obtained through differentinitial raw materials, and an existing synthetic route is enriched.