13207-66-4

Basic information

• Product Name: 5-Amino-8-hydroxyquinoline
• Synonyms: 5-AMINO-8-HYDROXYQUINOLINE;5-Amino-8-hydroxyqui;5-Amino-8-hydroxyquinoline HClsalt
• CAS NO: 13207-66-4
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17
• EINECS: 1533716-785-6
• Mol File: 13207-66-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 408.3 °C at 760 mmHg
• Flash Point: 200.7 °C
• Appearance: /
• Density: 1.363g/cm³
• Vapor Pressure: 3E-07mmHg at 25°C
• Refractive Index: 1.759
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 5-Amino-8-hydroxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-8-hydroxyquinoline(13207-66-4)
• EPA Substance Registry System: 5-Amino-8-hydroxyquinoline(13207-66-4)

Safety Data

• Hazardous Substances Data: 13207-66-4(Hazardous Substances Data)

Usage

General Description

5-Amino-8-hydroxyquinoline is a chemical compound known for its multi-functional applications. It falls under the group of organic compounds known as aminoquinolines and quinolones, distinguished by a quinoline bearing an amino group. 5-Amino-8-hydroxyquinoline is utilized in the field of coordination chemistry as it forms complexes with transition metals, such as copper, which can exhibit anticancer properties. Promising results from studies conducted also indicate its role in inhibiting the growth of certain bacteria, suggesting potential antibiotic uses. It has a yellowish appearance and should be handled carefully as it can cause skin irritation, eye damage, and respiratory irritation.

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

Synthetic route

nitroxoline (4008-48-4) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol for 3.5h; Schlenk technique; Inert atmosphere;	98%
With sodium dithionite In tetrahydrofuran; water at 55℃; for 0.25h; Inert atmosphere;	63%
With 5%-palladium/activated carbon; hydrazine hydrate In water; isopropyl alcohol for 7h; Reflux;	50.8%

5-Nitroso-8-hydroxyquinoline hydrochloride (63450-86-2) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With sodium hydroxide; sodium dithionite In water at 40 - 45℃;	83%
With sodium dithionite; sulfuric acid; sodium hydroxide Inert atmosphere;

5-nitroso-8-hydroxyquinoline (3565-26-2) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With hydrogenchloride; tin In water for 6h; Reflux;	79.87%
With nickel; acetone Hydrogenation;
With ethanol; nickel Hydrogenation;

5,8-quinolinoquinone 5-oxime (109701-95-3) + phenylhydrazine (100-63-0) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
at 100℃;

5-nitroquinoline (607-34-1) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With sulfate solution elektrolytische Reduktion;

p-<(8-hydroxy-5-quinolyl)azo>benzenesulphonamide (16588-39-9) → 5-amino-8-hydroxyquinoline (13207-66-4) + sulfanilamide (63-74-1)

Conditions	Yield
In water; N,N-dimethyl-formamide for 1.5h; electrolysis at dropping mercury electrode;

5-nitroquinoline (607-34-1) + sulfuric acid (7664-93-9) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
Electrolysis;

5-nitroso-8-oxy-quinoline → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With phenylhydrazine
With hydrogen sulfide; ammonia

5-nitroso-quinolin-8-ol hydrochloride → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

5-nitroso-quinolin-8-ol sulfate → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With ammonium hydroxide; sodium hydrogensulfite

-<4 azo 5>-<8-oxy-quinoline> → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

hydrochloride of 5-nitroso-8-oxy-quinoline → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

8-hydroxy-5-hydroxyamino-quinoline-6-sulfonic acid + ammonia (7664-41-7) + Na2S2O4 → 5-amino-8-hydroxyquinoline (13207-66-4)

phenetol-<4 azo 5>-<8-oxy-quinoline> → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With hydrogenchloride; tin

hydrogenchloride (7647-01-0) + 5,8-quinolinoquinone 5-oxime (109701-95-3) + tin dichloride → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
Reaktion des Hydrochlorids;

hydrogenchloride (7647-01-0) + 5-[(E)-2-(4'-ethoxyphenyl)-1-(diazenyl)]quinolin-8-ol (75907-28-7) + tin → 5-amino-8-hydroxyquinoline (13207-66-4)

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid (574-70-9) + HCl-salt tin dichloride solution → 5-amino-8-hydroxyquinoline (13207-66-4) + 4-aminobenzene sulfonic acid (121-57-3)

5-amino-8-hydroxyquinoline dihydrochloride (21302-43-2) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
With sodium hydrogencarbonate In water pH=7.5;	740 mg

nitroxoline (4008-48-4) → 5-amino-8-hydroxyquinoline (13207-66-4) + 5-(hydroxyamino)quinolin-8-ol

Conditions	Yield
With hydrazine hydrate In chloroform for 2h; chemoselective reaction;

8-quinolinol (148-24-3) → 5-amino-8-hydroxyquinoline (13207-66-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 4 °C 2: sodium dithionite; sulfuric acid; sodium hydroxide / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid; sodium nitrite 2: sulfuric acid; nitric acid 3: hydrogenchloride; tin(ll) chloride / water / 80 °C View Scheme

5-amino-8-hydroxyquinoline (13207-66-4) + 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (189306-94-3) → 5-acetyl-2-ethyl-4-((8-hydroxyquinolin-5-yl)amino)-6-phenylpyridazin-3(2H)-one (720717-72-6)

Conditions	Yield
In ethanol at 20℃; for 40h;	90%

5-amino-8-hydroxyquinoline (13207-66-4) + 6,7-dimethoxy-4-chloroquinazoline (13790-39-1) → 4-[(3'-hydroxyquiline)-5]-amino-6,7-dimethoxyquinazoline

Conditions	Yield
In ethanol for 4h; Reflux;	85%

5-amino-8-hydroxyquinoline (13207-66-4) + 4-ethylbenzylaldehyde (4748-78-1) → C18H16N2O

Conditions	Yield
In ethanol for 4h; Reflux;	83%

5-amino-8-hydroxyquinoline (13207-66-4) + benzaldehyde (100-52-7) → 5-(benzylidene)amino-8-hydroxyquinoline (1236049-61-8)

Conditions	Yield
With formic acid In ethanol at 85℃; for 5h;	80.6%
With formic acid In ethanol at 83℃; for 4h;	78.2%
With sulfuric acid In ethanol Reflux;

pyridine-4-carbaldehyde (872-85-5) + 5-amino-8-hydroxyquinoline (13207-66-4) → 5-((pyridin-4-ylmethylene)amino)quinolin-8-ol

Conditions	Yield
With formic acid In ethanol at 85℃; for 5h;	80.2%

5-amino-8-hydroxyquinoline (13207-66-4) + 9-anthracene aldehyde (642-31-9) → 5-(9-anthranylene)-8-hydroxyquinoline

Conditions	Yield
In methanol for 6h; Reflux;	71%

5-amino-8-hydroxyquinoline (13207-66-4) + salicylaldehyde (90-02-8) → C17H13NO2

Conditions	Yield
With formic acid In ethanol at 70 - 80℃; for 3h;	69%

5-amino-8-hydroxyquinoline (13207-66-4) → 5,8-quinolinedione (10470-83-4)

Conditions	Yield
With sodium dichromate; sulfuric acid In dichloromethane; water at 0℃; for 1h;	61%
	50%
With potassium dichromate; sulfuric acid
With sulfuric acid In water at 0℃; for 0.5h;

5-amino-8-hydroxyquinoline (13207-66-4) + acryloyl chloride (814-68-6) → N-(8-hydroxy-quinolin-5-yl)-acrylamide (65930-22-5)

Conditions	Yield
With triethylamine In dichloromethane	50%

5-amino-8-hydroxyquinoline (13207-66-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (8-((tert-butyldimethylsilyl)oxy)quinolin-5-amine)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 4h;	40%
With 1H-imidazole In dichloromethane

pyridine-2-carbaldehyde (1121-60-4) + 5-amino-8-hydroxyquinoline (13207-66-4) → 5-[(pyridin-2-ylmethylene)-amino]quinolin-8-ol

Conditions	Yield
With acetic acid In ethanol for 3h; Reflux;	7%

5-amino-8-hydroxyquinoline (13207-66-4) + acetic anhydride (108-24-7) → N-(8-hydroxyquinolin-5-yl)acetamide (65618-64-6)

Conditions	Yield
With diethyl ether; sodium acetate

5-amino-8-hydroxyquinoline (13207-66-4) + benzaldehyde (100-52-7) + 2-oxo-propionic acid (127-17-3) → 6-hydroxy-2-phenyl-[1,7]phenanthroline-4-carboxylic acid

Conditions	Yield
With ethanol

5-amino-8-hydroxyquinoline (13207-66-4) + benzoyl chloride (98-88-4) → N-(8-hydroxyquinolin-5-yl)benzamide (92868-24-1)

Conditions	Yield
With pyridine

5-amino-8-hydroxyquinoline (13207-66-4) + benzoyl chloride (98-88-4) → 5-benzoylamino-8-benzoyloxy-quinoline (65618-63-5)

Conditions	Yield
With alkaline solution

5-amino-8-hydroxyquinoline (13207-66-4) + propionic acid anhydride (123-62-6) → N-(8-hydroxy-[5]quinolyl)-propionamide (75653-04-2)

5-amino-8-hydroxyquinoline (13207-66-4) + 2-(diethylamino)ethyl chloride (100-35-6) → 5-(2-diethylamino-ethylamino)-quinolin-8-ol; dihydrochloride

Conditions	Yield
With benzene

5-amino-8-hydroxyquinoline (13207-66-4) → 5-bromo-8-hydroxyquinoline (1198-14-7)

Conditions	Yield
Diazotization;
With water; hydrogen bromide Diazotization.Beim Erhitzen einer Diazoniumsalz-Loesung mit Kupfer(I)-bromid;

Upstream product

• 3565-26-2 5-nitroso-8-hydroxyquinoline 
• 607-34-1 5-nitroquinoline 
• 7664-93-9 sulfuric acid 
• 7664-41-7 ammonia 
• 7647-01-0 hydrogenchloride 
• 109701-95-3 5,8-quinolinoquinone 5-oxime 
• 75907-28-7 5-[(E)-2-(4'-ethoxyphenyl)-1-(diazenyl)]quinolin-8-ol 
• 63450-86-2 5-Nitroso-8-hydroxyquinoline hydrochloride 
• 148-24-3 8-quinolinol 
• 4008-48-4 nitroxoline 
• 21302-43-2 5-amino-8-hydroxyquinoline dihydrochloride 
• 574-70-9 (E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid 
• 16588-39-9 p-<(8-hydroxy-5-quinolyl)azo>benzenesulphonamide 
• 100-63-0 phenylhydrazine 

Downstream Products

• 92868-24-1 N-(8-hydroxyquinolin-5-yl)benzamide 
• 65618-63-5 5-benzoylamino-8-benzoyloxy-quinoline 
• 10470-83-4 5,8-quinolinedione 
• 1198-14-7 5-bromo-8-hydroxyquinoline 
• 18633-05-1 6,7-Dibrom-5,8-dihydrochinolin-5,8-dion 
• 65930-22-5 N-(8-hydroxy-quinolin-5-yl)-acrylamide 
• 1236049-63-0 5-(4-fluorobenzylidene)-8-hydroxylquinoline 
• 1236049-62-9 C₁₆H₁₁ClN₂O 
• 1236049-61-8 5-(benzylidene)amino-8-hydroxyquinoline 
• 1236049-65-2 C₁₇H₁₄N₂O₂ 
• 1236049-64-1 C₁₆H₁₁BrN₂O 
• 35976-63-7 6-phenethylamino-quinoline-5,8-dione 
• 908078-38-6 C₁₇H₁₄N₂O₄ 

Relevant articles and documents

Four tetra-nuclear lanthanide complexes based on 8-hydroxyquinolin derivatives: magnetic refrigeration and single-molecule magnet behaviour

Four tetra-nuclear lanthanide complexes: {[Ln4(L)6(tmhd)4(μ3-OH)2]·mH2O} (Ln = Gd (1, m = 0), Tb (2, m = 3), Dy (3, m = 0), Ho (4, m = 0); L = 5-((pyridin-4-ylmethylene)amino)quinolin-8-ol, tmhd = 2,2,6,6-tetramethylheptane-3,5-dione) were fabricated and structurally characterized. Compounds 1-4 are isostructural and belong to the monoclinic system with space group P21/n. The cores of the complexes contain a tetranuclear arrangement of LnIII ions, which is bridged by the two pyramidal μ3-OH- ions, and the four LnIII ions are precisely coplanar. The magnetic study reveals that 1 exhibits cryogenic magnetic refrigeration property (-ΔSm = 20.85 J K-1 kg-1), whereas compound 3 exhibits slow relaxation of the magnetization.

Catechol O-methyltransferase. 2. In vitro inhibition by substituted 8-hydroxyquinolines.

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G-quadruplex and duplex DNA binding studies of novel Ruthenium(II) complexes containing ascididemin ligands

In this paper, three new Ruthenium(II) polypyridyl complexes containing ascididemin (ASC) as main ligand have been synthesized and characterized. Their interactions with different G-quadruplex (Htelo, c-myc and c-kit) (Htelo: human telomeric DNA, c-myc: cellular-myelocytomatosis viral oncogene, c-kit: oncogene c-kit promoter sequences) and duplex (ds26) DNA sequences were comparatively studied with the free ligand ASC by a series of spectroscopic techniques including UV–vis (ultraviolet-visible) spectroscopy, FID (fluorescent intercalator displacement) assay, and FRET (fluorescence resonance energy transfer) melting assay. Molecular docking studies were also performed to support the binding mode of the compounds with G-quadruplex DNA. Results indicated that [Ru(bpy)2ASC]·(PF6)2 (1), [Ru(phen)2ASC]·(PF6)2 (2), [Ru(tatp)2ASC]·(PF6)2 (3) (bpy = 2,2′?bipyridine, phen = 1,10?phenanthroline, tatp = 1,4,8,9?tetra?aza?triphenylene) and ASC can effectively bind G-quadruplex and duplex DNA and stabilization ability lies in the order 3 > 2 > 1 > ASC. Complex 3 was determined to be the most promising candidate for further in vitro studies and potential anticancer drug.