21302-43-2

Basic information

• Product Name: 5-Amino-8-quinolinol dihydrochloride
• Synonyms: 5-AMINO-8-HYDROXYQUINOLINE DIHYDROCHLORIDE;5-AMINO-8-QUINOLINOL DIHYDROCHLORIDE;5-Amino-8-hydroquinoline dihydrochloride;5-Amino-8-hydroxyquinoline2HCl;8-Quinolinol, 5-amino-, dihydrochloride;5-AMINO-8-HYDROXYQUINOLINE DIHYDROCHLORIDE 97+%;5-Amino-8-hydroxyquinoline dihydrochloride,5-Amino-8-quinolinol dihydrochloride;5-AMino-8-hydroxyquinoline dihydrochloride 95%
• CAS NO: 21302-43-2
• Molecular Formula: C₉H₈N₂O*2ClH
• Molecular Weight: 233.09
• Product Categories: Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Aminoquinolines;Hydroxyquinolines;Quinolines
• Mol File: 21302-43-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 279 °C (dec.)(lit.)
• Boiling Point: 442.6 °C at 760 mmHg
• Flash Point: 221.5 °C
• Appearance: /
• Density: 1.363g/cm3
• Vapor Pressure: 1.9E-08mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: almost transparency
• CAS DataBase Reference: 5-Amino-8-quinolinol dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-8-quinolinol dihydrochloride(21302-43-2)
• EPA Substance Registry System: 5-Amino-8-quinolinol dihydrochloride(21302-43-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 21302-43-2(Hazardous Substances Data)

Usage

Description

5-Amino-8-quinolinol dihydrochloride is a crystalline powder that serves as an important intermediate in the synthesis of various organic compounds and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
5-Amino-8-quinolinol dihydrochloride is used as a key intermediate for the synthesis of several pharmaceutical compounds, including 5-acetamido-8-hydroxyquinoline hydrochloride, 5-(p-tolylsulfonylimino)quinolin-8-one, and 5,8-quinolinesemiquinone via ferric chloride oxidation. These synthesized compounds have potential applications in the development of new drugs and therapies.
Used in Organic Synthesis:
5-Amino-8-quinolinol dihydrochloride is used as a versatile building block in organic synthesis for the preparation of various quinoline-based derivatives. Its unique structure allows for further functionalization and modification, making it a valuable component in the synthesis of complex organic molecules and potential drug candidates.
Used in Research and Development:
5-Amino-8-quinolinol dihydrochloride is utilized in research and development laboratories for the study of quinoline chemistry, its derivatives, and their potential applications in various fields, such as medicinal chemistry, materials science, and agrochemicals. Its use in research helps to advance the understanding of quinoline-based compounds and their properties, leading to the discovery of new applications and improvements in existing ones.

InChI:InChI=1/C9H8N2O.2ClH/c10-7-3-4-8(12)9-6(7)2-1-5-11-9;;/h1-5,12H,10H2;2*1H

Upstream product

• 4008-48-4 nitroxoline 
• 63450-86-2 5-Nitroso-8-hydroxyquinoline hydrochloride 
• 148-24-3 8-quinolinol 

Downstream Products

• 95911-99-2 4,5-dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>quinoline-2-carboxylic acid 
• 95912-10-0 C₁₉H₁₁N₃O₃ 
• 6541-19-1 6,7-dichloroquinoline-5,8-dione 
• 18633-05-1 6,7-Dibrom-5,8-dihydrochinolin-5,8-dion 
• 213027-68-0 8-(benzyloxy)quinolin-5-amine 
• 1096018-11-9 N-(8-hydroxyquinolin-5-yl)-N'-(4-nitrophenyl) thiourea 
• 1262633-05-5 4-fluoro-N-(8-hydroxyquinolin-5-yl)benzenesulfonamide 
• 1262633-07-7 N-(8-hydroxyquinolin-5-yl)-[1,1'-biphenyl]-4-sulfonamide 
• 92437-91-7 N-(8-hydroxyquinolin-5-yl)benzenesulfonamide 
• 1352798-72-1 1-(3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-yl)-3-(8-(2,3-diaminopyridin-4-yloxy)quinolin-5-yl)urea 
• 1352798-71-0 1-(3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-yl)-3-(8-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)quinolin-5-yl)urea 
• 1352798-49-2 1-(8-((2-amino-3-nitropyridin-4-yl)oxy)quinolin-5-yl)-3-(3-(tert-butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl)urea 
• 13207-66-4 5-amino-8-hydroxyquinoline 
• 1372123-87-9 5-[N,N-di(4-methoxybenzyl)amino]-8-hydroxyquinoline 

Relevant articles and documents

Quinone imines with a fused azine ring: I. Synthesis and hydrochlorination of 5-(p-tolylsulfonylimino)quinolin-8-one

5-(p-Tolylsulfonylimino)quinolin-8-one was synthesized, and its reaction with hydrogen chloride was studied. The reaction leads to formation of 7-chloro-8-hydroxy-5-(p-tolylsulfonylamino)quinoline hydrochloride.

Substituted oxines inhibit endothelial cell proliferation and angiogenesis

Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2) and sirtuin 1 (SIRT1). Structure-activity relationship study (SAR) of nitroxoline offered many surprises where minor modifications yielded oxine derivatives with increased potency against human umbilical vein endothelial cells (HUVEC), but with entirely different as yet unknown mechanisms. For example, 5-nitrosoquinolin-8-ol (33) inhibited HUVEC growth with sub-micromolar IC50, but did not affect MetAP2 or MetAP1, and it only showed weak inhibition against SIRT1. Other sub-micromolar inhibitors were derivatives of 5-aminoquinolin-8-ol (34) and 8-sulfonamidoquinoline (32). A sulfamate derivative of nitroxoline (48) was found to be more potent than nitroxoline with the retention of activities against MetAP2 and SIRT1. The bioactivity of the second hit, micromolar HUVEC and MetAP2 inhibitor carbamate 22 was improved further with an SAR study culminating in carbamate 24 which is a nanomolar inhibitor of HUVEC and MetAP2. The Royal Society of Chemistry 2012.