6-Fluoro-2,4-dihydroxyquinoline

Base Information

• Chemical Name: 6-Fluoro-2,4-dihydroxyquinoline
• CAS No.: 1677-37-8
• Molecular Formula: C9H6FNO2
• Molecular Weight: 179.151
• Hs Code.: 2933499090
• Mol file: 1677-37-8.mol

Synonyms:Carbostyril,6-fluoro-4-hydroxy- (7CI,8CI);6-Fluoro-2,4-dihydroxyquinoline;6-Fluoro-2,4-quinolinediol;

Chemical Property of 6-Fluoro-2,4-dihydroxyquinoline

Chemical Property:

• Refractive Index: 1.628
• Boiling Point: 402.1 °C at 760 mmHg
• Flash Point: 197 °C
• PSA: 53.35000
• Density: 1.477 g/cm³
• LogP: 1.78510

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Fluoroquinoline-2,4-diol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Fluoro-2,4-dihydroxyquinoline

There total 7 articles about 6-Fluoro-2,4-dihydroxyquinoline 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: 93.6%

4-fluoroaniline (371-40-4) + diethyl malonate (105-53-3) → 6-fluoro-4-hydroxy-1H-quinolin-2-one (1677-37-8)

Guidance literature:

With aluminum (III) chloride; Eaton′s reagent; at 90 ℃; for 6h; Inert atmosphere;

Reference yield: 85.0%

malonic acid (141-82-2) + 4-fluoroaniline (371-40-4) → 6-fluoro-4-hydroxy-1H-quinolin-2-one (1677-37-8)

Guidance literature:

In N,N-dimethyl-formamide; for 0.05h; microwave irradiation;

DOI:10.1016/j.bmcl.2006.09.082

Reference yield: 75.0%

N1,N3-bis(4-fluorophenyl)malonamide (1677-29-8) → 6-fluoro-4-hydroxy-1H-quinolin-2-one (1677-37-8)

Guidance literature:

With polyphosphoric acid; at 140 - 150 ℃; for 6h;

DOI:10.1016/j.cclet.2010.01.017

upstream raw materials:

malonic acid

4-fluoroaniline

N¹,N³-bis(4-fluorophenyl)malonamide

diethyl malonate

Downstream raw materials:

C₁₅H₉FN₄O₄

C₁₆H₉FN₄O₂

3,3-dibenzyl-6-fluoro-4-hydroxy-3,4-dihydro-1H-quinolin-2-one

3,3-dibenzyl-6-fluoro-1H-quinoline-2,4-dione

Refernces

• 1、 Arya, Kapil,Agarwal, Manish. "Microwave prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones". . p. 86 - 93. Retrieved 2007.
• 2、 Abdelhamid, Dalia,Abourehab, Mohammed A. S.,Abuo‐Rahma, Gamal El‐Din A.,Badr, Mohamed,Hassan, Abdelfattah,Hassan, Heba A.. "Design, synthesis, in vitro antiproliferative evaluation and in silico studies of new VEGFR-2 inhibitors based on 4-piperazinylquinolin-2(1H)-one scaffold". . . Retrieved 2022/01/31.
• 3、 Hassan, Abdelfattah,Badr, Mohamed,Hassan, Heba A.,Abdelhamid, Dalia,Abuo‐Rahma, Gamal El‐Din A.. "Novel 4-(piperazin-1-yl)quinolin-2(1H)-one bearing thiazoles with antiproliferative activity through VEGFR-2-TK inhibition". . . Retrieved 2021/05/10.