2-Hydroxyquinoline

Base Information

• Chemical Name: 2-Hydroxyquinoline
• CAS No.: 59-31-4
• Deprecated CAS: 493-62-9
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 29334900
• European Community (EC) Number: 200-420-6,274-516-1
• NSC Number: 156783,554
• UNII: 803BHY7QWU
• DSSTox Substance ID: DTXSID1058769
• Nikkaji Number: J4.598E
• Wikipedia: 2-Quinolone
• Wikidata: Q27095480
• Pharos Ligand ID: KB62MC58SY5W
• Metabolomics Workbench ID: 49826
• ChEMBL ID: CHEMBL186422
• Mol file: 59-31-4.mol

Synonyms:2-hydroxyquinoline

Chemical Property of 2-Hydroxyquinoline

Chemical Property:

• Appearance/Colour: white to light purple or purple-brownish powder
• Vapor Pressure: 5.67E-05mmHg at 25°C
• Melting Point: 198-199 °C(lit.)
• Refractive Index: 1.595
• Boiling Point: 346.7 °C at 760 mmHg
• PKA: -0.31, 11.76(at 20℃)
• Flash Point: 200.6 °C
• PSA: 32.86000
• Density: 1.188 g/cm³
• LogP: 1.52810
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: alcohol: soluble(lit.)
• Water Solubility.: 1.052g/L(20 oC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 198

Purity/Quality:

99.9% ^*data from raw suppliers

2-Hydroxyquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-41-37/38-22
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=O)N2
• Recent ClinicalTrials: Evidence Based Management of Acute Biliary Pancreatitis
• Uses: 2-Hydroxyquinoline was used to obtain the design of the platinum(IV) complexes with intense bands shifted towards longer wavelengths. The Pt(IV) complexes are inert stable prodrugs that were photoactivated to produce Pt(II) species with promising anticancer activity.

Technology Process of 2-Hydroxyquinoline

There total 282 articles about 2-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: 96.0%

quinoline (91-22-5) → 2-quinolone (59-31-4,70254-42-1,493-62-9)

Guidance literature:

With water; chloroacetic acid ethyl ester; In ethyl acetate; for 0.416667h; Concentration; Reagent/catalyst; Solvent; Wavelength; Microwave irradiation;

Reference yield: 92.0%

N-phenylcinnamamide (3056-73-3) → 2-quinolone (59-31-4,70254-42-1,493-62-9)

Guidance literature:

With aluminum (III) chloride; In chlorobenzene; at 90 - 110 ℃; for 4h;

DOI:10.1016/j.bioorg.2020.103791

Reference yield: 85.0%

1-(p-methoxybenzoyloxy)-2(1H)-quinolone (1404369-03-4) → 2-quinolone (59-31-4,70254-42-1,493-62-9) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

In methanol; water; Quantum yield; UV-irradiation; Photolysis;

DOI:10.1002/chem.201104065

upstream raw materials:

quinoline

2-Chloroquinoline

Quinoline N-oxide

3,4-dihydro-2(1H)-quinolone

Downstream raw materials:

2-(piperazin-1-yl)quinoline

N-(4-cholro-2-quinolyl)-4-chloro-2-quinolone

4-chloro-2-tosyloxyquinoline

6-methoxy-2(1H)-quinolinone

Refernces

• 1、 Bhuyan, Samuzal,Chhetri, Karan,Hossain, Jagir,Jana, Saibal,Mandal, Susanta,Roy, Biswajit Gopal. "Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides". . p. 5049 - 5055. Retrieved 2021/07/29.
• 2、 Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling. "Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones". . p. 5599 - 5604. Retrieved 2021/08/01.