30958-68-0

Basic information

• Product Name: 2-amino-1-oxo-1,2-dihydroquinolinium
• CAS NO: 30958-68-0
• Molecular Formula: C₉H₉N₂O
• Molecular Weight: 161.18
• Mol File: 30958-68-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-amino-1-oxo-1,2-dihydroquinolinium(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-1-oxo-1,2-dihydroquinolinium(30958-68-0)
• EPA Substance Registry System: 2-amino-1-oxo-1,2-dihydroquinolinium(30958-68-0)

Safety Data

• Hazardous Substances Data: 30958-68-0(Hazardous Substances Data)

Usage

General Description

2-amino-1-oxo-1,2-dihydroquinolinium is a chemical compound with the molecular formula C9H8N2O. It is a derivative of quinoline and is classified as a quaternary ammonium salt. 2-amino-1-oxo-1,2-dihydroquinolinium has a yellow to orange color and is commonly used as a dye intermediate in the production of various organic pigments and dyes. It can also be used as a catalyst in organic synthesis reactions. Additionally, 2-amino-1-oxo-1,2-dihydroquinolinium has been studied for its potential pharmacological properties, including its antibacterial and antifungal activities. Overall, this chemical compound has a variety of industrial and research applications.

Upstream product

• 65246-03-9 (1-oxy-[2]quinolyl)-carbamic acid ethyl ester 
• 51796-60-2 2-Azidoquinoline 1-oxide 
• 580-22-3 2-aminoquinoline 
• 23862-56-8 quinolin-2-yl-carbamic acid ethyl ester 
• 51991-49-2 1-cyano-2-(2'-nitrophenyl)ethene 

Downstream Products

• 34884-59-8 6-(toluene-4-sulfonyloxy)-quinolin-2-ylamine 
• 93014-22-3 toluene-4-sulfonic acid-(2-amino-[3]quinolyl ester) 

Relevant articles and documents

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

Ring Contraction of 2-Azidoquinoline and Quinoxaline 1-Oxides

Thermal ring contraction of 2-azidoquinoline 1-oxide with loss of nitrogen did not lead to the desired 2-cyano-1-hydroxyindole.Instead, 2-cyanoisatogen (9), 2,2'-dicyano-3,3'-bis (10), and 2-aminoquinoline 1-oxide (7) were formed.The mechanism is believed to involve an intermolecular addition to the intermediate cis-o-nitrosocinnamonitrile formed in a concerted ring-opening nitrogen loss, i.e., not involving a nitrene intermediate.In accord with this, both 2-azido-4-methylquinoline 1-oxide and 2-azidoquinoxaline 1-oxide give the expected 2-cyano-1-hydroxy-3-methylindole (18) and 2-cyano-1-hydroxybenzimidazole (26), respectively.