4-Hydroxyquinoline

Base Information

• Chemical Name: 4-Hydroxyquinoline
• CAS No.: 611-36-9
• Molecular Formula: C9H7NO
• Molecular Weight: 145.161
• Hs Code.: 29334900
• European Community (EC) Number: 210-268-2
• NSC Number: 263800,3183
• UNII: M1O131WXFO
• DSSTox Substance ID: DTXSID50209980
• Nikkaji Number: J387.250E,J7.017C
• Wikipedia: 4-Quinolone
• Wikidata: Q27098240
• Metabolomics Workbench ID: 50270
• ChEMBL ID: CHEMBL1232567
• Mol file: 611-36-9.mol

Synonyms:4-hydroxyquinoline

Chemical Property of 4-Hydroxyquinoline

Chemical Property:

• Appearance/Colour: light yellow and off-white crystal powder
• Vapor Pressure: 0.0115mmHg at 25°C
• Melting Point: 200-202 °C(lit.)
• Refractive Index: 1.595
• Boiling Point: 261.5 °C at 760 mmHg
• PKA: 2.23, 11.28(at 20℃)
• Flash Point: 122.3 °C
• PSA: 33.12000
• Density: 1.188 g/cm³
• LogP: 1.94040
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in methanol.
• Water Solubility.: 溶于醇，微溶于水
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 145.052763847
• Heavy Atom Count: 11
• Complexity: 198

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxyquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C=CN2
• Uses: 4-Hydroxyquinolineis a hydroxylated quinoline derivative with antimicrobial activity. 4-Hydroxyquinoline showed growth-inhibitory effects against intestinal bacteria. 4-Hydroxyquinoline act as sacrifi cial scavengers of the photogenerated oxygen species and has been shown to prevent the photodegradation of riboflavin. 4-Hydroxyquinoline is a medical raw material.

Technology Process of 4-Hydroxyquinoline

There total 30 articles about 4-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: 99.0%

4-(phenylmethoxy)quinoline (101273-58-9) → quinolin-4-ol (611-36-9)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; chemoselective reaction; Schlenk technique; Irradiation; Inert atmosphere;

DOI:10.1021/acs.joc.7b02775

Reference yield: 97.0%

4-hydroxy-3-quinoline carboxylic acid (34785-11-0) → quinolin-4-ol (611-36-9)

Guidance literature:

In diphenylether; for 1h; Reflux;

DOI:10.1002/cmdc.201900243

Reference yield: 88.3%

7-chloro-1,2,3,4-tetrahydroquinolin-4-one (21617-15-2) → 7-chloro-4-hydroxylquinoline (86-99-7) + quinolin-4-ol (611-36-9)

Guidance literature:

upstream raw materials:

Quinoline N-oxide

dichloroacethyl chloride

4(1H)-quinolinone

2,3-dihydroquinolin-4(1H)-one

Downstream raw materials:

4-hydroxyquinoline-3-carbaldehyde

4-mercaptoquinoline

4-chloroquinoline

3-bromo-4-hydroxyquinoline

Refernces

Synthesis of 3-substituted-4-hydroxyquinoline N-oxides from the Baylis-Hillman adducts of o-nitrobenzaldehydes

10.1016/S0040-4020(02)01518-1

The study focuses on the synthesis of 3-substituted-4-hydroxyquinoline N-oxides from Baylis–Hillman adducts derived from o-nitrobenzaldehydes. The key chemicals used in the study include trifluoroacetic acid, trifllic acid, and various Baylis–Hillman adducts such as 1b–f, which are derived from methyl vinyl ketone, phenyl vinyl sulfone, and ethyl acrylate. These chemicals serve the purpose of facilitating the reaction that yields the desired quinoline N-oxide derivatives. The study also explores the reaction mechanism, suggesting that N-hydroxyisoxazoline acts as a key intermediate in the process. The use of triflic acid was found to increase the acidity of the reaction medium, which was crucial for obtaining the quinoline N-oxides in reasonable yields. The study provides experimental evidence supporting the proposed reaction mechanism and successfully synthesizes several 3-substituted-4-hydroxyquinoline N-oxides, which are valuable synthetic intermediates.

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

10.1021/acs.joc.0c01662

Caixia Xie, Di Yang, Xinfeng Wang, and Chen Ma present a novel transition-metal-free cascade reaction for synthesizing 4-quinolone derivatives. The method involves Michael addition and Truce-Smiles rearrangement, yielding a broad scope of 4-quinolones in moderate-to-excellent yields under mild conditions. The study explores the optimization of reaction conditions, substrate scope, and scalability, demonstrating the potential for synthesizing densely functionalized 4-quinolone derivatives with applications in biomedical research. The use of sulfonamides through Truce-Smiles rearrangement offers a new approach to constructing heterocyclic compounds, with ongoing research focusing on applying this strategy to synthesize bioactive heterocyclic compounds.