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:

98% HPLC ^*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-methoxyquinoline

1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one

4-bromoquinoline

3-bromo-4-(4'-methoxyphenyl)quinoline

Refernces

• 1、 Lee, Myung Koo,Hwang, Bang Yeon,Lee, Seon A,Oh, Gab Jin,Choi, Woo Hoi,Hong, Seong Su,Lee, Kyong Soon,Ro, Jai Seup. "1-methyl-2-undecyl-4(1H)-quinolone as an irreversible and selective inhibitor of type B monoamine oxidase.". . p. 409 - 411. Retrieved 2003.
• 2、 Yuan, Qing,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun. "Copper-Catalyzed Chemoselective Cyclization Reaction of 2-Isocyanoacetophenone: Synthesis of 4-Hydroxyquinoline Compounds". . p. 1279 - 1284. Retrieved 2020/01/22.
• 3、 Todorov, Aleksandar R.,Wirtanen, Tom,Helaja, Juho. "Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism". . p. 13756 - 13767. Retrieved 2017/12/26.