2-Hydroxyquinoline-4-carboxylic acid

Base Information

• Chemical Name: 2-Hydroxyquinoline-4-carboxylic acid
• CAS No.: 15733-89-8
• Molecular Formula: C10H7 N O3
• Molecular Weight: 189.17
• Hs Code.: 2933499090
• European Community (EC) Number: 239-827-9,628-092-3
• NSC Number: 3564
• UNII: Z1Q2K479UQ
• DSSTox Substance ID: DTXSID40166250
• Nikkaji Number: J28.307J
• Wikidata: Q27123129
• Metabolomics Workbench ID: 58053
• ChEMBL ID: CHEMBL2048387
• Mol file: 15733-89-8.mol

Synonyms:2-Hydroxyquinoline-4-carboxylic acid;15733-89-8;84906-81-0;2-oxo-1,2-dihydroquinoline-4-carboxylic acid;2-Hydroxycinchoninic acid;2-Hydroxy-4-quinolincarboxylic acid;4-Carboxycarbostyril;2-oxo-1H-quinoline-4-carboxylic acid;Cinchoninic acid, 2-hydroxy-;4-Quinolinecarboxylic acid, 1,2-dihydro-2-oxo-;2-oxocinchoninic acid;2-hydroxy-4-quinolinecarboxylic acid;Cinchocaine Impurity B;1,2-Dihydro-2-oxoquinoline-4-carboxylic acid;2-HYDROXYQUINOLINE-4-CARBOXYLICACID;2-Hydroxy-quinoline-4-carboxylic acid;4-Quinolinecarboxylic acid, 2-hydroxy-;EINECS 239-827-9;MFCD00023942;UNII-Z1Q2K479UQ;AI3-61768;Z1Q2K479UQ;CHEBI:52045;1,2-dihydro-2-oxo-4-Quinolinecarboxylic acid;2-oxo-4-quinolinecarboxylic acid;NSC-3564;Enamine_001230;Cambridge id 5133898;Oprea1_034107;SCHEMBL662652;IFLab1_001493;SCHEMBL8729784;CHEMBL2048387;MFSHNFBQNVGXJX-UHFFFAOYSA-;DTXSID40166250;NSC3564;HMS1397H20;HMS1416D19;BCP28536;CCG-1662;NSC 3564;BBL008901;MFCD00464512;STK078430;STK709494;IFLAB-BB F1918-0080;2-Hydroxyquinolinecarboxylic acid-(4);AKOS000104068;AKOS000266346;2(1H)-Oxoquinoline-4-carboxylic acid;AC-1861;CCG-104483;CS-W015953;SB67443;SDCCGMLS-0065426.P001;NCGC00246893-01;AC-23085;AS-12503;LS-53794;SY020050;Quinoline-4-carboxylic acid, 2(1H)-oxo-;2-Hydroxyquinoline-4-carboxylic acid, 97%;AM20070290;BB 0221218;BB 0221230;EU-0001998;FT-0612590;FT-0612638;FT-0648864;H1016;2-Oxo-1,2-dihydro-4-quinolinecarboxylic acid;EN300-00825;2-oxidanylidene-1H-quinoline-4-carboxylic acid;D78174;2-Oxo-1,2-dihydro-4-quinolinecarboxylic acid #;A809841;A841008;SR-01000403999;SR-01000597059;SR-01000403999-1;SR-01000597059-1;SR-01000597059-2;W-108003;Q27123129;Z56795730;F0346-1608;2-Oxo-1,2-dihydroquinoline-4-carboxylic acid, AldrichCPR;CINCHOCAINE HYDROCHLORIDE IMPURITY B [EP IMPURITY];Cinchocaine Hydrochloride Imp. B (EP): 2-Hydroxyquinoline-4-

Chemical Property of 2-Hydroxyquinoline-4-carboxylic acid

Chemical Property:

• Appearance/Colour: Orange crystalline powder
• Vapor Pressure: 3.07E-07mmHg at 25°C
• Melting Point: 350°C
• Boiling Point: 403.6 °C at 760 mmHg
• PKA: 2.76±0.20(Predicted)
• Flash Point: 197.9 °C
• PSA: 70.42000
• Density: 1.429 g/cm³
• LogP: 1.63860
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 189.042593085
• Heavy Atom Count: 14
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

1,?2-?Dihydro-?2-?oxo-4-?quinolinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC(=O)N2)C(=O)O
• Uses: 1,?2-?Dihydro-?2-?oxo-4-?quinolinecarboxylic Acid is a chemical constituent of vinegar Schisandra chinensis and is used as a indicator reagent in marking security documents.

Technology Process of 2-Hydroxyquinoline-4-carboxylic acid

There total 40 articles about 2-Hydroxyquinoline-4-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: 97.3%

malonic acid (141-82-2) + indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → 2-hydroxyquinoline-4-carboxylic acid (15733-89-8,84906-81-0)

Guidance literature:

With sodium acetate; acetic acid; for 6h; Reagent/catalyst; Reflux; Large scale;

Reference yield: 79.0%

4-carboxyquinoline 1-oxide (40614-43-5) → Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + 2-quinolone-4-carboxylic acid (15733-89-8)

Guidance literature:

In methanol; for 0.666667h; Irradiation;

DOI:10.1248/cpb.28.1157

Reference yield: 65.0%

1-acetyl-1H-indole-2,3-dione (574-17-4) → 2-hydroxyquinoline-4-carboxylic acid (15733-89-8,84906-81-0)

Guidance literature:

With sodium hydroxide; In water; for 0.05h; microwave irradiation;

DOI:10.1080/00397910500184719

upstream raw materials:

C₆H₄NCH₂CHCCH₂

1-acetyl-1H-indole-2,3-dione

2-chloroquinoline-4-carboxylic acid

ethyl ester of 2-chlorocinchoninic acid

Downstream raw materials:

2-(n-butyloxy)-4-(n-butyloxycarbonyl)-quinoline

1-(n-butyl)-4-(n-butyloxycarbonyl)-2-oxo-1,2-dihydroquinoline

2-hydroxy-4-quinoline

2-hydroxy-4-quinoline

Refernces

• 1、 Feldman, Ken S.,Coca, Adiel. "Synthesis of the pentacyclic core of lihouidine". . p. 2136 - 2138. Retrieved 2008.
• 2、 Bindu,Vijayalakshmi,Manikandan. "Discovery, synthesis and molecular substantiation of N-(benzo[d]thiazol-2-yl)-2-hydroxyquinoline-4-carboxamides as anticancer agents". . . Retrieved 2019.
• 3、 Egli,Richter. "-". . p. 499. Retrieved 1957.
• 4、 Li, Wenlong,Xu, Feijie,Shuai, Wen,Sun, Honghao,Yao, Hong,Ma, Cong,Xu, Shengtao,Yao, Hequan,Zhu, Zheying,Yang, Dong-Hua,Chen, Zhe-Sheng,Xu, Jinyi. "Discovery of Novel Quinoline-Chalcone Derivatives as Potent Antitumor Agents with Microtubule Polymerization Inhibitory Activity". . p. 993 - 1013. Retrieved 2019.
• 5、 Baba, Yassir Filali,Boukir, Abdellatif,Chahdi, Fouad Ouazzani,Essassi, El Mokhtar,G?kce, Halil,H?kelek, Tuncer,Hayani, Sonia,Jasinski, Jerry P.,Kaur, Manpreet,Rodi, Youssef Kandri,Sebbar, Nada Kheira. "Syntheses of novel 2-oxo-1,2-dihydroquinoline derivatives: Molecular and crystal structures, spectroscopic characterizations, Hirshfeld surface analyses, molecular docking studies and density functional theory calculations". . . Retrieved 2020/05/29.