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8-Hydroxyquinoline

Base Information Edit
  • Chemical Name:8-Hydroxyquinoline
  • CAS No.:148-24-3
  • Deprecated CAS:123574-67-4,24804-14-6
  • Molecular Formula:C9H7NO
  • Molecular Weight:203.241
  • Hs Code.:2933.40
  • European Community (EC) Number:205-711-1
  • NSC Number:615011,402623,285166,2039
  • UN Number:2811
  • UNII:5UTX5635HP
  • DSSTox Substance ID:DTXSID5020730
  • Nikkaji Number:J2.960B
  • Wikipedia:8-hydroxyquinoline
  • Wikidata:Q270162
  • NCI Thesaurus Code:C80862
  • RXCUI:110
  • Metabolomics Workbench ID:57149
  • ChEMBL ID:CHEMBL310555
  • Mol file:148-24-3.mol
8-Hydroxyquinoline

Synonyms:8 Hydroxyquinoline;8 Hydroxyquinoline Sulfate;8 Oxyquinoline;8 Quinolinol;8-Hydroxyquinoline;8-Hydroxyquinoline Sulfate;8-Oxyquinoline;8-Quinolinol;Bioquin;Chinosol;Khinozol;Leioderm;Oxine;Oxyquinol;Oxyquinoline;Oxyquinoline Potassium Sulfate (2:1);Oxyquinoline Sulfate;Quinosol;Sulfate, 8-Hydroxyquinoline;Sulfate, Oxyquinoline;Superol

Suppliers and Price of 8-Hydroxyquinoline
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • 8-Hydroxyquinoline
  • 500g
  • $ 195.00
  • TCI Chemical
  • 8-Quinolinol >99.0%(GC)(T)
  • 25g
  • $ 19.00
  • TCI Chemical
  • 8-Quinolinol >99.0%(GC)(T)
  • 500g
  • $ 87.00
  • SynQuest Laboratories
  • 8-Hydroxyquinoline 99%
  • 500 g
  • $ 56.00
  • SynQuest Laboratories
  • 8-Hydroxyquinoline 99%
  • 100 g
  • $ 18.00
  • SynQuest Laboratories
  • 8-Hydroxyquinoline 99%
  • 1 kg
  • $ 90.00
  • Sigma-Aldrich
  • 8-Hydroxyquinoline crystalline
  • 100g
  • $ 89.10
  • Sigma-Aldrich
  • 8-Hydroxyquinoline for synthesis. CAS 148-24-3, molar mass 145.16 g/mol., for synthesis
  • 8202611000
  • $ 179.00
  • Sigma-Aldrich
  • 8-Hydroxyquinoline for synthesis
  • 1 kg
  • $ 171.12
  • Sigma-Aldrich
  • 8-Hydroxyquinoline GR for analysis ACS,Reag. Ph Eur. CAS 148-24-3, molar mass 145.16 g/mol., GR for analysis Reag. Ph Eur
  • 1070980250
  • $ 279.00
Total 287 raw suppliers
Chemical Property of 8-Hydroxyquinoline Edit
Chemical Property:
  • Appearance/Colour:Cream-colored crystals 
  • Vapor Pressure:0.221Pa at 25℃ 
  • Melting Point:70-73 °C(lit.) 
  • Refractive Index:1.4500 (estimate) 
  • Boiling Point:267 °C at 760 mmHg 
  • PKA:5.017(at 20℃) 
  • Flash Point:143.1 °C 
  • PSA:33.12000 
  • Density:1.26 g/cm3 
  • LogP:1.94040 
  • Storage Temp.:Store at RT. 
  • Sensitive.:Light Sensitive 
  • Solubility.:0.56g/l 
  • Water Solubility.:INSOLUBLE 
  • XLogP3:2
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:145.052763847
  • Heavy Atom Count:11
  • Complexity:138
  • Transport DOT Label:Poison
Purity/Quality:

99%, *data from raw suppliers

8-Hydroxyquinoline *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn 
  • Hazard Codes:Xn,Xi 
  • Statements: 22-68-36/37/38 
  • Safety Statements: 45-36/37/39-26-36 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Nitrogen Compounds -> Quinolines
  • Canonical SMILES:C1=CC2=C(C(=C1)O)N=CC=C2
  • Chemical Composition and Structure Oxyquinoline, also known as 8-Hydroxyquinoline, is a heterocyclic phenol. It can form salts, such as Oxyquinoline Sulfate. Oxyquinoline contains a quinoline core with a hydroxyl group (–OH) attached to the eighth carbon atom.
  • Uses Oxyquinoline and its derivatives have been extensively studied for their pharmacological properties and corrosion inhibition capabilities. They are considered privileged structures in drug discovery due to their diverse biological activities.
    Oxyquinoline and its derivatives have diverse applications, including as stabilizers for hydrogen peroxide in cosmetic formulations, as metal ion chelators for neuroprotection, anticancer agents, inhibitors of 2OG-dependent enzymes, anti-HIV agents, antifungal agents, and corrosion inhibitors for metals like steel, aluminum, copper, and magnesium alloys.
    Oxyquinoline and its derivatives have remarkable antimicrobial activities and corrosion inhibition properties. They form coordination complexes with metal atoms and ions, making them effective corrosion inhibitors for various metals in corrosive environments. The development of new derivatives of oxyquinoline for corrosion inhibition purposes continues to be an active area of research and development.
  • General Description 8-Hydroxyquinoline is a versatile heterocyclic compound that serves as a key scaffold in medicinal chemistry, demonstrating applications in the synthesis of bioactive molecules with antioxidant and anticancer properties. Its derivatives, such as Mannich bases, have shown significant growth-inhibitory effects on various cancer cell lines, with structural modifications enhancing their potency. Additionally, 8-hydroxyquinoline participates in reductive cyclization reactions to form novel heterocyclic compounds, highlighting its utility in drug discovery and chemical synthesis.
Technology Process of 8-Hydroxyquinoline

There total 108 articles about 8-Hydroxyquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
glycerol; With sulfuric acid; copper(II) sulfate; calcium oxide; for 1h; Reflux;
2-amino-phenol; for 0.333333h;
With 2-hydroxynitrobenzene; at 130 - 140 ℃; Concentration;
Guidance literature:
With piperidine; carbon monoxide; palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 50 ℃; for 24h; under 52505.3 Torr;
DOI:10.1016/j.tet.2011.02.003
Guidance literature:
With i-Amyl alcohol; ozone; In water; at -0.1 ℃;
Refernces Edit

Facile preparation of tetrahydro-5H-pyrido[1,2,3-de]-1,4-benzoxazines via reductive cyclization of 2-(8-quinolinyloxy)ethanones and their antioxidant activity

10.1016/j.bmcl.2013.09.088

The study presents a facile method for the preparation of tetrahydro-5H-pyrido[1,2,3-de]-1,4benzoxazines, a novel family of heterocyclic compounds, through the Pd/C-catalyzed reductive cyclization of 1-aryl-2-(8-quinolinyloxy)ethanones. These compounds are of interest due to their potential antioxidant activity and presence in pharmacologically active compounds. The research explores the scope of this reductive cyclization and evaluates the antioxidant activities of the synthesized products. The chemicals used in the study include 8-hydroxyquinoline, α-haloketones, and Pd/C as a catalyst for the cyclization reaction, as well as various substituted 1-aryl-2-(quinolin-8-yloxy)ethanones to synthesize a range of tricyclic compounds. The purpose of these chemicals was to synthesize the target heterocyclic compounds and assess their potential as antioxidants, which could have applications in pharmaceuticals, pesticides, and other industries.

Synthesis and structure-activity relationship study of 8-hydroxyquinoline- derived Mannich bases as anticancer agents

10.1016/j.ejmech.2010.03.008

The research study on the synthesis and structure-activity relationship of 8-hydroxyquinoline-derived Mannich bases as potential anticancer agents. The purpose of the study was to explore the growth-inhibitory effects of these compounds on various human carcinoma cell lines and to understand the impact of structural modifications on their potency. The researchers synthesized a series of Mannich bases and assessed their activity against cell lines including HeLa, BT483, SKHep, and CE81T using the MTT assay. The conclusions drawn from the study emphasized that the 8-hydroxyquinoline scaffold is crucial for activity, and certain structural modifications, such as the introduction of flexible fragments and specific substituents, significantly enhanced the growth-inhibitory effects. Notably, compound 25 emerged as the most active against HeLa and BT483 cells, while compounds 19 and 26 showed potent effects on SKHep and CE81T cells, respectively. The study utilized a variety of chemicals in the synthesis process, including 8-hydroxyquinoline, phenol, 3-hydroxypyridine, 1-naphthol, and various substituted phenylsulfonyl and piperazine derivatives. The 3D-QSAR analysis further revealed that both steric and electronic effects contributed equally to the growth inhibition, providing valuable insights for future structural optimizations.

Reaction of phenyl glycidyl ether with some heterocycles

10.1007/s10593-008-0093-6

The study focused on the reaction of phenyl glycidyl ether with various heterocyclic compounds to synthesize new compounds with potential biological activity. The chemicals used included 5,5-dimethylhydantoin, morpholine, benzotriazole, benzimidazole, pyrrolidone, phthalimide, and 8-hydroxyquinoline. These heterocyclic compounds served as reactants to form N-(2-hydroxy-3-phenoxypropyl) derivatives, which are of interest due to their potential to contain pharmacophoric fragments that could lead to the discovery of new biologically active substances. The purpose of the study was to develop a one-stage method for synthesizing these derivatives, which could be applied in preparative chemistry and contribute to the development of new drugs.

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