2836-41-1

Basic information

• Product Name: Quinoline, 2-(2-fluorophenyl)-
• CAS NO: 2836-41-1
• Molecular Formula: C15H10FN
• Molecular Weight: 223.25
• Mol File: 2836-41-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Quinoline, 2-(2-fluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 2-(2-fluorophenyl)-(2836-41-1)
• EPA Substance Registry System: Quinoline, 2-(2-fluorophenyl)-(2836-41-1)

Safety Data

• Hazardous Substances Data: 2836-41-1(Hazardous Substances Data)

Upstream product

• 445-27-2 2'-Fluoroacetophenone 
• 552-89-6 2-nitro-benzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 445-26-1 1-(2-fluorophenyl)ethanol 
• 2005-43-8 2-bromoquinoline 
• 1993-03-9 o-fluorophenylboronic acid 
• 58106-57-3 (E)-3-(2-aminobenzene)acrylonitrile 

Downstream Products

• 1346939-41-0 2-(4'-methyl-[1,1'-biphenyl]-2-yl)quinoline 

Relevant articles and documents

Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.

Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach

Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.

Pd-Catalyzed Tandem Reaction of 2-Aminostyryl Nitriles with Arylboronic Acids: Synthesis of 2-Arylquinolines

A novel palladium-catalyzed protocol for the synthesis of 2-arylquinolines via tandem reaction of 2-aminostyryl nitriles with arylboronic acids has been developed with good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2-arylquinolines compared to classical condensation reaction of (E)-2-aminostyryl aryl ketones. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular cyclization and dehydration to quinoline ring.