8-Hydroxyquinoline

Base Information

• 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

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

Chemical Property of 8-Hydroxyquinoline

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:

98% ^*data from raw suppliers

8-Hydroxyquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• 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.

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:

Reference yield: 96.31%

2-amino-phenol (95-55-6) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 8-quinolinol (148-24-3,24804-14-6)

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;

Reference yield: 83.0%

5,7-diiodo-8-hydroxyquinoline (83-73-8) → 8-quinolinol (148-24-3,24804-14-6)

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

Reference yield: 78.0%

quinoline (91-22-5) → 8-quinolinol (148-24-3,24804-14-6)

Guidance literature:

With i-Amyl alcohol; ozone; In water; at -0.1 ℃;

upstream raw materials:

quinoline

8-amino quinoline

8-methoxyquinoline

8-hydroxyquinoline-4-carboxylic acid

Downstream raw materials:

8-Hydroxyquinoline-N-oxide

7-((benzo[d]thiazol-2-ylamino)(phenyl)methyl)quinolin-8-ol

7-[α-(1H-benzimidazol-2-ylamino)-benzyl]-quinolin-8-ol

8-ethoxyquinoline

Refernces

• 1、 Inoue et al.. "-". . p. 430. Retrieved 1954.
• 2、 Vogler, Arnd. "Photolysis of Zn(8-quinolinolate)2(H2O)2 in non-aqueous solution. Photoactivation of hydrolysis". . p. 82 - 83. Retrieved 2014.
• 3、 Franks, Andrew T.,Franz, Katherine J.. "A prochelator with a modular masking group featuring hydrogen peroxide activation with concurrent fluorescent reporting". . p. 11317 - 11320. Retrieved 2014.
• 4、 King,Sherred. "-". . p. 415. Retrieved 1942.
• 5、 Frere, F. J.. "". . p. 4362 - 4362. Retrieved 1933.
• 6、 Lippmann. "-". . p. 439. Retrieved 1887.
• 7、 Dickens, Marina G.,Franz, Katherine J.. "A prochelator activated by hydrogen peroxide prevents metal-induced amyloid β aggregation". . p. 59 - 62. Retrieved 2010.
• 8、 Tackett, James E.,Sawyer, Donald T.. "Properties and infrared spectra in the potassium bromide region of 8-quinolinol and its metal chelates". . p. 692 - 696. Retrieved 1964.
• 9、 Yuchi, Akio,Muranaka, Hiroshi,Yamada, Shinkichi,Tanaka, Motoharu. "Dissociation of μ-Oxo-bis and μ-Oxo-bis in Chlorobenzene". . p. 1560 - 1563. Retrieved 1980.
• 10、 Cardwell, T. J.,Magee, R. J.. "". . p. 180 - 188. Retrieved 1966.