2-Chloroquinoline-4-carboxylic acid

Base Information

• Chemical Name: 2-Chloroquinoline-4-carboxylic acid
• CAS No.: 5467-57-2
• Molecular Formula: C10H6ClNO2
• Molecular Weight: 207.616
• Hs Code.: 2933499090
• European Community (EC) Number: 679-916-3
• NSC Number: 25654
• DSSTox Substance ID: DTXSID40282368
• Wikidata: Q72459317
• ChEMBL ID: CHEMBL1887535
• Mol file: 5467-57-2.mol

Synonyms:2-chloroquinoline-4-carboxylic acid;5467-57-2;4-Quinolinecarboxylic acid, 2-chloro-;2-CHLORO-4-CARBOXY QUINOLINE;2-Chloro-quinoline-4-carboxylic acid;MFCD00023940;NSC25654;2-Chloro-4-quinolinecarboxylic acid;2-chlorocinchoninic acid;A-Chloro cinchoninic acid;Oprea1_333438;Oprea1_493520;SCHEMBL57542;MLS000713994;CHEMBL1887535;DTXSID40282368;HMS2744K20;AMY23012;BBL011721;NSC 25654;NSC-25654;STK387506;AKOS000291599;2-Chloro-4-quinolinecarboxylic acid #;CS-W015258;PB18416;AC-23006;SMR000273475;SY051158;TS-02965;A7935;BB 0241837;C1703;FT-0635745;EN300-17872;2-Chloro-4-quinolinecarboxylic acid, AldrichCPR;SR-01000596891;SR-01000596891-1;W-203063;Z57052891;159113-47-0

Chemical Property of 2-Chloroquinoline-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 4.35E-06mmHg at 25°C
• Melting Point: 35-37°C
• Refractive Index: 1.69
• Boiling Point: 368.7 °C at 760 mmHg
• PKA: 2.17±0.10(Predicted)
• Flash Point: 176.8 °C
• PSA: 50.19000
• Density: 1.469 g/cm³
• LogP: 2.58640
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 207.0087061
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

2-Chloroquinoline-4-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC(=N2)Cl)C(=O)O
• Uses: 2-Chloroquinoline-4-carboxylic Acid is an intermediate used to prepare dimethyl(naphthalenecarbonyl)aminobenzoic acids as potent and selective EP4 antagonists.

Technology Process of 2-Chloroquinoline-4-carboxylic acid

There total 10 articles about 2-Chloroquinoline-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: 87.5%

2-quinolone-4-carboxylic acid (15733-89-8) → 2-chloroquinoline-4-carboxylic acid (5467-57-2)

Guidance literature:

With trichlorophosphate; for 1h; Reflux;

Reference yield: 87.0%

2-hydroxyquinoline-4-carboxylic acid (15733-89-8,84906-81-0) → 2-chloroquinoline-4-carboxylic acid (5467-57-2)

Guidance literature:

With trichlorophosphate; for 24h; Heating / reflux;

Reference yield: 67.0%

4-Bromo-2-chloro-quinoline (83674-64-0) + formyl acetic anhydride (2258-42-6) → 2-chloroquinoline-4-carboxylic acid (5467-57-2)

Guidance literature:

4-Bromo-2-chloro-quinoline; formyl acetic anhydride; With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80 - 90 ℃; for 3.5h; Inert atmosphere;

With hydrogenchloride; In water; pH=Ca. 4 - 6;

DOI:10.1080/00397911.2010.528851

upstream raw materials:

4-carboxyquinoline 1-oxide

2-hydroxyquinoline-4-carboxylic acid

ethyl ester of 2-chlorocinchoninic acid

2-quinolone-4-carboxylic acid

Downstream raw materials:

2-(n-butyloxy)-4-quinolinecarboxylic acid

2-phenylsulfanyl-quinoline-4-carboxylic acid

2-amino-quinoline-4-carboxylic acid

2-hydroxyquinoline-4-carboxylic acid

Refernces

• 1、 -. "Quinoline substituted chalcone compound as well as preparation method and application thereof". Paragraph 0027; 0100; 0104. . Retrieved 2019/03/29.
• 2、 Shivaraj, Yellappa,Naveen, Malenahalli H.,Vijayakumar, Giriyapura R.,Kumar, Doyijode B. Aruna. "Design, synthesis and antibacterial activity studies of novel quinoline carboxamide derivatives". . p. 241 - 245. Retrieved 2013/07/25.