54012-92-9

Usage

Uses

Used in Pharmaceutical Industry:
8-Amino-1,2,3,4-tetrahydroquinoline is used as a building block for the synthesis of pharmaceutical compounds due to its unique chemical structure and potential to contribute to the development of new drugs.
Used in Coordination Chemistry:
In coordination chemistry, 8-Amino-1,2,3,4-tetrahydroquinoline serves as a ligand, playing a crucial role in the formation and stabilization of metal complexes, which can have various applications in catalysis, sensing, and materials science.
Used in Organic Electronics:
8-Amino-1,2,3,4-tetrahydroquinoline is used in the development of organic electronic devices such as organic light-emitting diodes (OLEDs) for its potential to enhance device performance and efficiency.
Used in Antimicrobial Applications:
8-Amino-1,2,3,4-tetrahydroquinoline is utilized for its antimalarial and antibacterial properties, offering a potential alternative in the treatment of infections caused by drug-resistant pathogens.
Used in Organic Photovoltaics:
In the field of renewable energy, 8-Amino-1,2,3,4-tetrahydroquinoline is employed in the design and fabrication of organic photovoltaics, contributing to the advancement of solar energy technology.

InChI:InChI=1/C9H12N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1,3,5,11H,2,4,6,10H2

Upstream product

• 1613-37-2 Quinoline N-oxide 
• 91-22-5 quinoline 
• 87866-74-8 benzophenone 1,2,3,4-tetrahydroquinolin-1-ylhydrazone 

Downstream Products

• 137469-86-4 8-(N-tert-Butoxycarbonylamino)-1,2,3,4-tetrahydroquinoline 
• 578-66-5 8-amino quinoline 
• 298182-02-2 C₂₉H₂₉N₅O₄S 
• 2759-25-3 2,3-diphenyl-6,7-dihydro-3H,5H-pyrido[1,2,3-de]quinoxaline 
• 110177-81-6 2-Hydroxymethyl-5,6-dihydro-imidazochinolin 
• 24246-26-2 5,6-dihydroimidazo(i,j)quinoline 

Relevant academic research and scientific papers

Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups

Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.

REARRANGEMENTS OF AROMATIC CARBONYL ARYLHYDRAZONES OF BENZENE, NAPHTHALENE, AND AZULENE

Aromatic carbonyl arylhydrazones have been shown to undergo two kinds of rearrangement in polyphosphoric acid both involving nitrogen-nitrogen bond cleavage.The first proceeds via insertion of the imine portion in the position ortho to the second nitrogen atom to give o-phenylenediamine intermediates: their evolution depends on the nature of the starting substrate.This reaction has been employed for synthesizing the quinoxalines (5) and the phenanthridines (11), and was demonstrated to be intramolecular.The second reaction path is a sigmatropic rearrangment exclusive to electron-rich aromatic carbonyl hydrazones.