Ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate
• CAS No.: 107555-38-4
• Molecular Formula: C₁₂H₉F₂NO₃
• Molecular Weight: 253.205
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID10383972
• Wikidata: Q82175819
• ChEMBL ID: CHEMBL4535294
• Mol file: 107555-38-4.mol

Synonyms:ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate;107555-38-4;ethyl 6,8-difluoro-4-oxo-1H-quinoline-3-carboxylate;6,8-Difluoro-4-hydroxyquinoline-3-carboxylic acid ethyl ester;Maybridge3_000305;Bionet2_000041;Oprea1_128487;ethyl 6,8-difluoro-4-hydroxy-3-quinolinecarboxylate;SCHEMBL6200613;CHEMBL4535294;DTXSID10383972;ETHYL6,8-DIFLUORO-4-HYDROXYQUINOLINE-3-CARBOXYLATE;HMS1364B19;HMS1431N19;6,8-Difluoro-4-hydroxy-quinoline-3-carboxylic acid ethyl ester;BBL028329;MFCD00173349;STK786668;AKOS000271248;CCG-233911;SB69302;IDI1_011692;BB 0241108;CS-0212501;VU0512660-1;5J-037;EN300-141924;A895422;F3173-0020;Z1737940705;3-Quinolinecarboxylic acid, 6,8-difluoro-4-hydroxy-, ethyl ester;6,8-Difluoro-4-hydroxy-quinoline-3-carboxylic acid ethyl ester;138595-83-2

Chemical Property of Ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 8.85E-05mmHg at 25°C
• Refractive Index: 1.537
• Boiling Point: 340ºC at 760 mmHg
• Flash Point: 159.4ºC
• PSA: 59.42000
• Density: 1.386g/cm3
• LogP: 2.39530
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 253.05504947
• Heavy Atom Count: 18
• Complexity: 397

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl6,8-difluoro-4-hydroxyquinoline-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CNC2=C(C1=O)C=C(C=C2F)F

Technology Process of Ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate

There total 2 articles about Ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate 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: 60.0%

diethyl 2-((2,4-difluorophenylamino)methylene)malonate (101830-90-4) → ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate (71083-11-9,107555-38-4)

Guidance literature:

In diphenylether; for 0.25h; Reflux;

DOI:10.1039/c8md00139a

Reference yield:

2,4-difluorophenylamine (367-25-9,76563-56-9) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate (71083-11-9,107555-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 3 h / 90 °C

2: diphenylether / 0.25 h / Reflux

In diphenylether;

DOI:10.1039/c8md00139a

Reference yield: 58.0%

ethyl 6,8-difluoro-4-hydroxyquinoline-3-carboxylate (71083-11-9,107555-38-4) → ethyl 4-chloro-6,8-difluoroquinoline-3-carboxylate (150258-20-1)

Guidance literature:

With trichlorophosphate; at 135 ℃; for 0.75h;

upstream raw materials:

diethyl 2-((2,4-difluorophenylamino)methylene)malonate

2,4-difluorophenylamine

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

ethyl 4-chloro-6,8-difluoroquinoline-3-carboxylate

Refernces

• 1、 Chen, Shuguang,Chen, Ran,He, Meizi,Pang, Ruifang,Tan, Zhiwu,Yang, Ming. "Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors". experimental part. p. 1948 - 1956. Retrieved 2009/05/26.