4-Hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid

Base Information

• Chemical Name: 4-Hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid
• CAS No.: 574-92-5
• Molecular Formula: C11H6 F3 N O3
• Molecular Weight: 257.169
• Hs Code.: 29334990
• European Community (EC) Number: 209-377-8,257-414-1
• DSSTox Substance ID: DTXSID60966092
• Nikkaji Number: J188.442E,J294.908C
• Wikidata: Q82948434
• ChEMBL ID: CHEMBL386466
• Mol file: 574-92-5.mol

Synonyms:574-92-5;4-Hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid;4-Hydroxy-7-trifluoromethyl-3-quinolinecarboxylic acid;51776-97-7;4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid;BRN 0249406;4-oxo-7-(trifluoromethyl)-1H-quinoline-3-carboxylic acid;EINECS 209-377-8;EINECS 257-414-1;1,4-Dihydro-4-oxo-7-(trifluoromethyl)quinoline-3-carboxylic acid;4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylic acid;C11H6F3NO3;4-Hydroxy-7-trifluoromethylquinoline-3-carboxylic acid;4-Hydroxy-7-(trifluoromethyl)-quinoline-3-carboxylic acid;3-Quinolinecarboxylic acid, 4-hydroxy-7-(trifluoromethyl)-;4-22-00-02331 (Beilstein Handbook Reference);C11-H6-F3-N-O3;MFCD00006771;MLS000552094;CHEMBL386466;SCHEMBL2978109;DTXSID60966092;HMS2171L11;HMS3311A07;BCP32423;BBL027607;CCG-16539;MFCD01912280;STK526599;STK584337;AKOS000268308;AKOS001629451;SB68800;SB71577;NCGC00246260-01;BP-12458;SMR000145818;TS-03465;LS-141650;CS-0155758;EU-0038081;FT-0632419;VU0561866-2;3-Carboxy-4-hydroxy-7-trifluoromethylquinoline;EN300-142646;SR-01000432012;J-640179;J-800180;SR-01000432012-1;W-203162;7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid;4-Hydroxy-7-(trifluoromethyl)quinoline-3-carboxylicacid;4-Hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid;F0910-1424;F3267-0070;Z1720962928;4-Hydroxy-7-(trifluoromethyl)-3-quinoline-carboxylic acid;1,4-Dihydro-4-oxo-7-(trifluoromethyl)-3-quinolinecarboxylic acid;4-Hydroxy-7-trifluoromethyl-3-quinolinecarboxylic acid, technical grade, 85%

Chemical Property of 4-Hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid

Chemical Property:

• Appearance/Colour: BEIGE CRYSTALLINE POWDER
• Melting Point: 259-260 °C (dec.)(lit.)
• Boiling Point: 354.7 °C at 760 mmHg
• PKA: 0.52±0.30(Predicted)
• Flash Point: 168.3 °C
• PSA: 70.42000
• Density: 1.55 g/cm³
• LogP: 2.65740
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 257.02997754
• Heavy Atom Count: 18
• Complexity: 416

Purity/Quality:

98%min ^*data from raw suppliers

4-Hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylic acid 97% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Quinolines
• Canonical SMILES: C1=CC2=C(C=C1C(F)(F)F)NC=C(C2=O)C(=O)O
• Uses: 4-Hydroxy-7-trifluoromethyl-3-quinolinecarboxylic acid was used in the preparation of (4-hydroxy-7-trifluoromethylquinolin-3-yl)formaldehyde.

Technology Process of 4-Hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid

There total 5 articles about 4-Hydroxy-7-(trifluoromethyl)quinoline-3-carboxylic acid 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: 97.7%

4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (391-02-6) → 4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylic acid (574-92-5)

Guidance literature:

With lithium hydroxide; In methanol; at 0 ℃; for 2.16667h;

DOI:10.1016/j.ejmech.2013.07.021

Reference yield: 65.0%

4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (391-02-6) + ethyl acetoacetate (141-97-9) → 4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylic acid (574-92-5) + ethyl 8-(trifluoromethyl)-2-methyl-4-oxo-4H-pyrano[3,2-c]quinolone 3-carboxylate

Guidance literature:

With sulfuric acid; In N,N-dimethyl-formamide; Reflux;

DOI:10.1134/S1070428020020219

Reference yield:

diethyl 2-({[3-(trifluoromethyl)phenyl]amino}methylidene)propanedioate (370-35-4) → 4-hydroxy-7-(trifluoromethyl)-3-quinolinecarboxylic acid (574-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl ether / Heating

2: 2 N NaOH / Heating

With sodium hydroxide; In diphenylether;

DOI:10.1021/jm980146x

upstream raw materials:

4-hydroxy-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester

diethyl 2-({[3-(trifluoromethyl)phenyl]amino}methylidene)propanedioate

3-trifluoromethylaniline

ethyl acetoacetate

Downstream raw materials:

4-Hydroxy-7-trifluormethyl-3-chinolincarbonsaeurechlorid

1-(4-cyanobenzyl)-4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid

1-(4-cyanobenzyl)-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid

1-(2,4-dichlorobenzyl)-4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid

Refernces

• 1、 Garudachari,Isloor, Arun M.,Satyanarayana,Fun, Hoong-Kun,Pavithra,Kulal, Ananda. "Design and regioselective synthesis of trifluoromethylquinolone derivatives as potent antimicrobial agents". . p. 422 - 432. Retrieved 2013/10/01.
• 2、 De, Dibyendu,Krogstad, Frances M.,Byers, Larry D.,Krogstad, Donald J.. "Structure-activity relationships for antiplasmodial activity among 7- substituted 4-aminoquinolines". . p. 4918 - 4926. Retrieved 2007/10/03.