6-Bromo-4-hydroxyquinoline-3-carboxylic acid

Base Information

• Chemical Name: 6-Bromo-4-hydroxyquinoline-3-carboxylic acid
• CAS No.: 98948-95-9
• Molecular Formula: C10H6BrNO3
• Molecular Weight: 268.067
• Hs Code.: 2933499090
• European Community (EC) Number: 804-515-9
• DSSTox Substance ID: DTXSID40912976
• Wikidata: Q72457042
• ChEMBL ID: CHEMBL216958
• Mol file: 98948-95-9.mol

Synonyms:6-Bromo-4-hydroxyquinoline-3-carboxylic acid;98948-95-9;302553-00-0;6-BROMO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID;6-bromo-4-oxo-1H-quinoline-3-carboxylic Acid;3-Quinolinecarboxylic acid, 6-bromo-1,4-dihydro-4-oxo-;3-QUINOLINECARBOXYLIC ACID, 6-BROMO-4-HYDROXY-;6-Bromo-4-hydroxyquinoline-3-carboxylicacid;MFCD01569278;6-BROMO-4-HYDROXY-3-QUINOLINECARBOXYLIC ACID;6-bromo-4-hydroxy-quinoline-3-carboxylic acid;Cambridge id 5870418;Oprea1_230624;Oprea1_277898;SCHEMBL741418;6-bromo-1,4-dihydro-4-oxoquinoline-3-carboxylic acid;CHEMBL216958;DTXSID40912976;GIUZUAUCCUFVKW-UHFFFAOYSA-N;BCP08176;CMA55300;CS-M0118;MFCD01909532;AKOS000273413;AKOS001595117;CCG-105910;PB19923;SB68897;AM804630;BP-20486;DS-11235;BB 0241160;FT-0645511;EN300-56471;6-Bromo-4-hydroxy-quinoline-3-carboxylic acid;AB00099868-01;A845930;J-650021;Z1259341128;6-bromanyl-4-oxidanylidene-1H-quinoline-3-carboxylic acid;6-Bromo-4-hydroxyquinoline-3-carboxylic acid, AldrichCPR;6-BROMO-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLICACID;6-Bromo-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid, AldrichCPR

Chemical Property of 6-Bromo-4-hydroxyquinoline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.58E-07mmHg at 25°C
• Refractive Index: 1.667
• Boiling Point: 412.069 °C at 760 mmHg
• Flash Point: 203.013 °C
• PSA: 70.42000
• Density: 1.805 g/cm³
• LogP: 2.40110
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 266.95311
• Heavy Atom Count: 15
• Complexity: 340

Purity/Quality:

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

6-Bromo-4-hydroxyquinoline-3-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=O)C(=CN2)C(=O)O
• Uses: It is used as a pharmaceutical intermediate.

Technology Process of 6-Bromo-4-hydroxyquinoline-3-carboxylic acid

There total 9 articles about 6-Bromo-4-hydroxyquinoline-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: 99.42%

6-bromo-4-hydroxyquinoline-3-carboxylic acid ethyl ester (122794-99-4) → 6-bromo-4-hydroxyquinoline-3-carboxylic acid (98948-95-9)

Guidance literature:

With water; sodium hydroxide; at 100 ℃; for 3h;

Reference yield: 96.0%

ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate (79607-23-1,122794-99-4) → 6-bromo-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (98948-95-9,302553-00-0)

Guidance literature:

With sodium hydroxide; for 3h; Reflux;

DOI:10.1021/acs.jmedchem.5b00515

Reference yield:

diethyl 2-((4-bromophenylamino)methylene)malonate (101937-44-4) → 6-bromo-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (98948-95-9,302553-00-0)

Guidance literature:

Multi-step reaction with 2 steps

1: various solvent(s) / 1 h / Heating

2: aq. NaOH / 1 h / Heating

With sodium hydroxide; In various solvent(s);

DOI:10.1021/jm050048t

upstream raw materials:

6-bromo-4-hydroxyquinoline-3-carboxylic acid ethyl ester

diethyl 2-((4-bromophenylamino)methylene)malonate

4-bromo-aniline

ethyl 6-bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylate

Downstream raw materials:

6-bromo-3-quinolinecarboxylic acid-4-ol

6-bromo-4-chloroquinoline

6-ethenyl-4-quinolinecarbonitrile

6-bromo-N-methyl-4-quinolinamine

Refernces

• 1、 Pike, Kurt G.,Barlaam, Bernard,Cadogan, Elaine,Campbell, Andrew,Chen, Yingxue,Colclough, Nicola,Davies, Nichola L.,De-Almeida, Camila,Degorce, Sebastien L.,Didelot, Myriam,Dishington, Allan,Ducray, Richard,Durant, Stephen T.,Hassall, Lorraine A.,Holmes, Jane,Hughes, Gareth D.,Macfaul, Philip A.,Mulholland, Keith R.,McGuire, Thomas M.,Ouvry, Gilles,Pass, Martin,Robb, Graeme,Stratton, Natalie,Wang, Zhenhua,Wilson, Joanne,Zhai, Baochang,Zhao, Kang,Al-Huniti, Nidal. "The Identification of Potent, Selective, and Orally Available Inhibitors of Ataxia Telangiectasia Mutated (ATM) Kinase: The Discovery of AZD0156 (8-{6-[3-(Dimethylamino)propoxy]pyridin-3-yl}-3-methyl-1-(tetrahydro-2 H-pyran-4-yl)-1,3-dihydro-2 H-imidazo[4,5- c]quinolin-2-one)". supporting information. p. 3823 - 3841. Retrieved 2018/05/14.
• 2、 Devine, William,Thomas, Sarah M.,Erath, Jessey,Bachovchin, Kelly A.,Lee, Patricia J.,Leed, Susan E.,Rodriguez, Ana,Sciotti, Richard J.,Mensa-Wilmot, Kojo,Pollastri, Michael P.. "Antiparasitic Lead Discovery: Toward Optimization of a Chemotype with Activity Against Multiple Protozoan Parasites". supporting information. p. 350 - 354. Retrieved 2017/03/17.