486-74-8

Basic information

• Product Name: QUINOLINE-4-CARBOXYLIC ACID
• Synonyms: AKOS BBS-00005335;AKOS BC-0749;4-QUINOLINECARBOXYLIC ACID;QUINOLINE-4-CARBOXYLIC ACID;TIMTEC-BB SBB003819;RARECHEM AL BE 0184;4-carboxyquinoline;cinchoninicacid
• CAS NO: 486-74-8
• Molecular Formula: C₁₀H₇NO₂
• Molecular Weight: 173.17
• EINECS: 207-640-1
• Product Categories: Quinolines, Quinazolines and derivatives;pharmacetical;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;Quinoline&Isoquinoline;Quinoline Derivertives;Quinolinecarboxylic Acids, etc.;Quinolines;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;Building Blocks;Heterocyclic Building Blocks
• Mol File: 486-74-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 254-255 °C(lit.)
• Boiling Point: 348.7 °C at 760 mmHg
• Flash Point: 164.7 °C
• Appearance: white to light yellow crystal powder
• Density: 1.339 g/cm³
• Vapor Pressure: 1.85E-05mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 1.03±0.10(Predicted)
• BRN: 5224
• CAS DataBase Reference: QUINOLINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: QUINOLINE-4-CARBOXYLIC ACID(486-74-8)
• EPA Substance Registry System: QUINOLINE-4-CARBOXYLIC ACID(486-74-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: GD3850000
• HazardClass: IRRITANT
• Hazardous Substances Data: 486-74-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Quinoline-4-carboxylic Acid for small therapeutic agent compounds.

Biochem/physiol Actions

4-Quinolinecarboxylic acid showed anti-tumor activity against L1210 leukemia and B16 melanoma.

Metabolic pathway

The bacterium which is isolated from soil enrichment culture degrades quinoline-4-carboxylic acid to give the two identified metabolites 2-oxo-1,2- dihydroquinoline-4-carboxylic acid and 8-hydroxy-2- oxo-2H-benzopyran-4-carboxylic acid.

InChI:InChI=1/C10H7NO2/c12-10(13)8-5-6-11-9-4-2-1-3-7(8)9/h1-6H,(H,12,13)/p-1

Upstream product

• 67-56-1 methanol 
• 4363-93-3 quinoline-4-carboxaldehyde 
• 151-50-8 potassium cyanide 
• 5467-61-8 ethyl ester of 2-chlorocinchoninic acid 
• 5323-57-9 quinoline-2,4-dicarboxylic acid 
• 108-95-2 phenol 
• 7647-01-0 hydrogenchloride 
• 2973-27-5 quinoline-4-carbonitrile 
• 7664-93-9 sulfuric acid 
• 53913-66-9 9-hydroxy-11-nor-cinchonan-10-oic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 64-19-7 acetic acid 
• 67-66-3 chloroform 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 21233-61-4 quinoline-4-carboxylic acid methyl ester 
• 10447-29-7 ethyl quinoline-4-carboxylate 
• 35035-57-5 4-methoxycarbonyl-1-methyl-quinolinium; iodide 
• 13337-69-4 (RS)-1,2,3,4-tetrahydroquinoline-4-carboxylic acid 
• 157915-68-9 2-amino-quinoline-4-carboxylic acid 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 91799-73-4 quinoline-4-carboxylic acid chloride hydrochloride 
• 580-18-7 3-hydroxyquinoline 
• 490-11-9 3,4-pyridinecarboxylic acid 

Relevant articles and documents

Synthesis and biological evaluation of novel 4-(6-substituted quinolin-4-yl)-N-aryl thiazol-2-amine derivatives as potential antimicrobial agents

Cyclocondensation reaction of 4-(2-bromoacetyl)quinolin-1-ium bromide (4a–d) with substituted arylthiourea, (5a–g) afforded 4-(6-substituted quinolin-4-yl)-N-aryl/pyridyl thiazol-2-amine (6a-ab). These newly synthesized derivatives were evaluated for in vitro antibacterial activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388) (Gram-negative strains), Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178) (Gram-positive strains) and in vitro antifungal activity against Aspergillus niger (ATCC 504) and Candida albicans (NCIM 3100). Compounds 6a, 6b, 6d, 6f, 6k, and 6l showed moderate to good antibacterial activity against S. albus. Ten derivatives 6c, 6q, 6r, 6s, 6t, 6v, 6w, 6x, 6y, and 6aa, showed moderate to good activity against A. niger. N-[4-(Quinolin-4-yl)-1,3-thiazol-2-yl]pyridin-2-amine presented comparable activity against A. niger with respect to standard drug Rouconazole.

Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation

A facile and efficient method for the preparation of 2-non-substituted quinoline-4-carboxylic acids is described via the Pfitzinger reaction of isatins with sodium pyruvate following consequent decarboxylation under microwave irradiation.

Facile, one-step production of niacin (vitamin B3) and other nitrogen-containing pharmaceutical chemicals with a single-site heterogeneous catalyst

Niacin (3-picolinic acid), which is extensively used as vitamin B 3 in foodstuffs and as a cholesterol-lowering agent, along with other oxygenated products of the picolines, 4-methylquinoline, and a variety of pyrimidines and pyridazines, may be produced in a single-step, environmentally benign fashion by combining single-site, open-structure, heterogeneous catalysts witha solid source of active oxygen, namely acetyl peroxyborate (APB), in the absence of an organic solvent. The high activities, selectivities, and the relatively mild conditions employed with this single-site heterogeneous catalyst, coupled with ease of transport, storage, and stability of the solid oxidant, augurs well for the future use of APB in conjunction with other open-structure, single-site catalysts for fine-chemical, pharmaceutical, and agrochemical applications.