Ethyl 8-fluoro-4-hydroxyquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 8-fluoro-4-hydroxyquinoline-3-carboxylate
• CAS No.: 71083-06-2
• Molecular Formula: C12H10FNO3
• Molecular Weight: 235.21
• Hs Code.: 2933499090
• European Community (EC) Number: 672-015-6
• DSSTox Substance ID: DTXSID40351700
• Wikidata: Q82128311
• Mol file: 71083-06-2.mol

Synonyms:ethyl 8-fluoro-4-hydroxyquinoline-3-carboxylate;63010-69-5;71083-06-2;ethyl 8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate;Ethyl 8-fluoro-4-hydroxy-3-quinolinecarboxylate;Ethyl 1,4-dihydro-8-fluoro-4-oxoquinoline-3-carboxylate;ethyl 8-fluoro-4-oxo-1H-quinoline-3-carboxylate;MFCD00052242;3-Quinolinecarboxylic acid, 8-fluoro-4-hydroxy-, ethyl ester;Maybridge1_000540;Oprea1_087885;Oprea1_472774;Oprea1_797370;F0850-4896;SCHEMBL1126279;HMS543A12;DTXSID40351700;AMY31042;BBL012990;BTB 02003;STK043561;STK151295;AKOS000669641;AKOS002250068;AB02175;AC-2910;CCG-233001;FS-1165;SB71649;SDCCGMLS-0065840.P001;SY003322;BB 0221936;EU-0073764;FT-0626156;5J-055;EN300-160126;A834143;ethyl 8-fluoro-4-hydroxyquinoline -3-carboxylate;SR-01000453236;J-521236;J-650055;SR-01000453236-1;ethyl8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate;3-Quinolinecarboxylicacid,8-fluoro-4-hydroxy-,ethyl ester;8-Fluoro-4-hydroxy-quinoline-3-carboxylic acid ethyl ester;8-fluoro-4-hydroxyquinoline-3-carboxylic acid ethyl ester;8-Fluoro-4-hydroxy-quinoline-3-carboxylic acid ethyl ester;Ethyl 8-fluoro-4-hydroxyquinoline-3-carboxylate, AldrichCPR;3-Quinolinecarboxylicacid,8-fluoro-1,4-dihydro-4-oxo-,ethyl ester

Chemical Property of Ethyl 8-fluoro-4-hydroxyquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 2.38mmHg at 25°C
• Melting Point: 217-219 °C
• Refractive Index: 1.498
• Boiling Point: 341.8 °C at 760 mmHg
• Flash Point: 160.5 °C
• PSA: 59.16000
• Density: 1.318 g/cm³
• LogP: 1.84390
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 235.06447134
• Heavy Atom Count: 17
• Complexity: 367

Purity/Quality:

98.5% ^*data from raw suppliers

Ethyl8-Fluoro-4-hydroxyquinoline-3-carboxylate ^*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: CCOC(=O)C1=CNC2=C(C1=O)C=CC=C2F

Technology Process of Ethyl 8-fluoro-4-hydroxyquinoline-3-carboxylate

There total 11 articles about Ethyl 8-fluoro-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: 100.0%

diethyl [(2-fluoroanilino)methylidene]malonate (63010-68-4) → ethyl 8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (71083-06-2)

Guidance literature:

In diphenylether; for 1h; Heating;

DOI:10.1135/cccc20060978

Reference yield: 14.0%

2-Fluoroaniline (348-54-9) + diethyl butylidenemalonate (13937-11-6) → ethyl 8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (71083-06-2)

Guidance literature:

2-Fluoroaniline; diethyl butylidenemalonate; at 140 ℃;

In diphenylether; at 190 ℃; Microwave irradiation;

DOI:10.1002/cmdc.201900283

Reference yield:

2-Fluoroaniline (348-54-9) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (71083-06-2)

Guidance literature:

2-Fluoroaniline; diethyl 2-ethoxymethylenemalonate; In toluene; for 5h; Reflux;

In Petroleum ether; at 280 ℃; for 3h;

DOI:10.1080/00397911.2015.1085576

upstream raw materials:

diethyl [(2-fluoroanilino)methylidene]malonate

2-Fluoroaniline

diethyl 2-ethoxymethylenemalonate

diethyl malonate

Downstream raw materials:

8-fluoroquinolin-4(1H)-one

ethyl 8-fluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

ethyl N-benzyl-8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Refernces

• 1、 Schramm, Simon,Agnetta, Luca,Bermudez, Marcel,Gerwe, Hubert,Irmen, Matthias,Holze, Janine,Littmann, Timo,Wolber, Gerhard,Tr?nkle, Christian,Decker, Michael. "Novel BQCA- and TBPB-Derived M1 Receptor Hybrid Ligands: Orthosteric Carbachol Differentially Regulates Partial Agonism". supporting information. p. 1349 - 1358. Retrieved 2019/07/12.
• 2、 Chen, Xinyu,Kl?ckner, Jessika,Holze, Janine,Zimmermann, Cornelia,Seemann, Wiebke K.,Schrage, Ramona,Bock, Andreas,Mohr, Klaus,Tr?nkle, Christian,Holzgrabe, Ulrike,Decker, Michael. "Rational design of partial agonists for the muscarinic M1 acetylcholine receptor". . p. 560 - 576. Retrieved 2015/01/30.