580-16-5

Basic information

• Product Name: 6-Hydroxyquinoline
• Synonyms: 1h-1,6-epoxyquinoline;QUINOLIN-6-OL;TIMTEC-BB SBB004117;AKOS 222-06;6-HYDROXYQUINOLINE;6-QUINOLINOL;6-HYDROXYQUINOLINE 98%;6-HYDROXYQUINOLINE (6-QUINOLINOL)
• CAS NO: 580-16-5
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 209-454-6
• Product Categories: Heterocyclic Series;Quinoline&Isoquinoline;Quinolines;Hydroxyquinolines;quinoline;Heterocycles
• Mol File: 580-16-5.mol
• Article Data: 48

Chemical Properties

• Melting Point: 188-190 °C(lit.)
• Boiling Point: 264.27°C (rough estimate)
• Flash Point: 143.1 °C
• Appearance: Beige to gray or brown/Powder
• Density: 1.1555 (rough estimate)
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 5.15, 8.90(at 20℃)
• Water Solubility: almost insoluble
• BRN: 113196
• CAS DataBase Reference: 6-Hydroxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxyquinoline(580-16-5)
• EPA Substance Registry System: 6-Hydroxyquinoline(580-16-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: VC4130000
• F: 8
• Hazardous Substances Data: 580-16-5(Hazardous Substances Data)

Usage

Description

6-Hydroxyquinoline, also known as 6-quinolol, is a white to light yellow crystal powder with the chemical formula C9H7NO. It is a monohydroxyquinoline that is quinoline substituted by a hydroxy group at position 6. 6-Hydroxyquinoline is an ideal photoacid system for exploring excited-state proton transfer (ESPT) reactions, making it a subject of interest in various research fields.

Uses

Used in Chemical Synthesis:
6-Hydroxyquinoline is used as a key intermediate in the synthesis of various organic compounds, particularly 2,6-substituted-benzo[d]thiazole analogs and 2,4-substituted-benzo[d]thiazole analogs. These analogs have potential applications in pharmaceuticals, agrochemicals, and other industries due to their unique chemical properties and biological activities.
Used in Photochemistry Research:
As an ideal photoacid system, 6-Hydroxyquinoline is used in the study of excited-state proton transfer (ESPT) reactions. Researchers utilize this compound to explore the excited-state proton transfer and geminate recombination processes, which are essential for understanding the behavior of various photochemical systems. This knowledge can be applied to develop new materials and technologies in areas such as solar energy conversion, sensors, and advanced imaging techniques.
Used in Pharmaceutical Industry:
6-Hydroxyquinoline and its derivatives have potential applications in the pharmaceutical industry due to their unique chemical properties. They can be used as building blocks for the development of new drugs with specific therapeutic targets. Additionally, their ability to participate in ESPT reactions makes them valuable in the design of drug delivery systems that can release active ingredients in a controlled manner upon exposure to light.
Used in Material Science:
The photochemical properties of 6-Hydroxyquinoline make it a promising candidate for the development of new materials with applications in optoelectronics, photovoltaics, and light-emitting devices. By understanding and exploiting the ESPT reactions in this compound, researchers can design materials with tailored properties for specific applications, such as light-harvesting systems or light-responsive switches.

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

Upstream product

• 91-22-5 quinoline 
• 5263-87-6 6-methoxy quinoline 
• 22883-85-8 6-ethoxy-quinoline 
• 4312-44-1 6-hydroxyquinoline-4-carboxylic acid 
• 27230-42-8 6-hydroxy-quinoline-5-carboxylic acid 
• 100-02-7 4-nitro-phenol 
• 123-30-8 4-amino-phenol 
• 51-66-1 4-methoxyacetanilide 
• 56-81-5 glycerol 
• 74-89-5 methylamine 
• 81336-59-6 quinolin-6-yl benzoate 
• 46046-37-1 6-quinolinediazonium 
• 87707-14-0 1a,7b-dihydrooxireno[2,3-f]quinoline 
• 7664-93-9 sulfuric acid 

Downstream Products

• 230-09-1 1H-[1,3]dioxino[5,4-f]quinoline 
• 4959-99-3 3H-pyrano[3,2-f]quinoline-3-one 
• 77717-71-6 6-hydroxyquinoline-5-carbaldehyde 
• 42379-06-6 4-(6-hydroxy-quinolin-5-ylazo)-benzenesulfonic acid 
• 24306-33-0 methyl quinolin-6-ylethanoate 
• 111359-52-5 4-[6]quinolylamino-phenol 
• 132982-92-4 N-(4-methylphenyl)quinolin-6-amine 
• 81336-59-6 quinolin-6-yl benzoate 
• 70682-98-3 N-phenylquinolin-6-amine 
• 426265-40-9 quinolin-6-yl 4-methylbenzene-1-sulfonate 
• 113060-97-2 [6]quinolyl-(2,4-dimethyl-phenyl)-amine 
• 5263-87-6 6-methoxy quinoline 
• 21979-59-9 6-methoxy-(N-methyl-quinolinium iodide) 
• 580-15-4 6-aminoquinoline 

Relevant articles and documents

Design, synthesis and biological evaluation of novel quinoline-based carboxylic hydrazides as anti-tubercular agents

In this study, seventeen novel quinoline-based carboxylic hydrazides were designed as potential anti-tubercular agents using molecular hybridization approach and evaluated in-silico for drug-likeness behavior. The compounds were synthesized, purified, and characterized using spectral techniques (like FTIR, 1H NMR, and Mass). The in-vitro anti-tubercular activity (against Mycobacterium tuberculosisH37Ra) and cytotoxicity against human lung fibroblast cells were studied. Among the tested hydrazides, four compounds (6h, 6j, 6l, and 6m) exhibited significant anti-tubercular activity with MIC values below 20?μg/mL. The two most potent compounds of the series, 6j and 6m exhibited MIC values 7.70 and 7.13?μg/mL, respectively, against M.?tuberculosis with selectivity index >26. Structure–activity relationship studies were performed for the tested compounds in order to explore the effect of substitution pattern on the anti-tubercular activity of the synthesized compounds.

Application of Electron-Rich Covalent Organic Frameworks COF-JLU25 for Photocatalytic Aerobic Oxidative Hydroxylation of Arylboronic Acids to Phenols

Visible-light-driven organic reactions are environmentally friendly green chemical transformations among which photosynthetic oxidative hydroxylation of arylboronic acids to phenols has attracted increasing research interest during the very recent years. Given the efficiency and reusability of heterogeneous catalysts, COF-JLU25, an electron-rich COF-based photocatalyst constructed by integrating electron-donating blocks 1,3,6,8-tetrakis(4-aminophenyl)pyrene (PyTA) and 4-[4-(4-formylmethyl)-2,5-dimethoxyphenyl] benzaldehyde (TpDA), was selected as a photocatalyst for the oxidative hydroxylation of arylboronic acids. In our studies, COF-JLU25 demonstrated excellent photocatalytic activity with high efficiency, robust reusability, and low catalyst loading, showcasing an application potential of previously underexplored COF-based photocatalyst composed solely of electron-rich units.

Biocatalytic Cross-Coupling of Aryl Halides with a Genetically Engineered Photosensitizer Artificial Dehalogenase

Devising artificial photoenzymes for abiological bond-forming reactions is of high synthetic value but also a tremendous challenge. Disclosed herein is the first photobiocatalytic cross-coupling of aryl halides enabled by a designer artificial dehalogenase, which features a genetically encoded benzophenone chromophore and site-specifically modified synthetic NiII(bpy) cofactor with tunable proximity to streamline the dual catalysis. Transient absorption studies suggest the likelihood of energy transfer activation in the elementary organometallic event. This design strategy is viable to significantly expand the catalytic repertoire of artificial photoenzymes for useful organic transformations.

Visible-light-promoted aerobic oxidative hydroxylation of arylboronic acids in water by hydrophilic organic semiconductor

A green and sustainable catalytic system was developed based on perylenediimide (PDI) organic semiconductor for the aerobic oxidative hydroxylation of arylboronic acids in aqueous solution with visible light. By using PDI-SN, a hydrophilic organic semiconductor, which can activate oxygen to produce superoxide radicals in aqueous solution, this reaction proceeds under ambient conditions: water as the solvent and air as the oxidant, giving various phenols as products with high yields. In contrast to methods using organic solvents, this novel process has the potential of green industrial application.