5278-43-3

Basic information

• Product Name: Quinoline, 3-methyl-2-phenyl-
• CAS NO: 5278-43-3
• Molecular Formula: C16H13N
• Molecular Weight: 219.286
• Mol File: 5278-43-3.mol
• Article Data: 55

Chemical Properties

• CAS DataBase Reference: Quinoline, 3-methyl-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 3-methyl-2-phenyl-(5278-43-3)
• EPA Substance Registry System: Quinoline, 3-methyl-2-phenyl-(5278-43-3)

Safety Data

• Hazardous Substances Data: 5278-43-3(Hazardous Substances Data)

Upstream product

• 123-38-6 propionaldehyde 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 529-23-7 o-aminobenzaldehyde 
• 93-55-0 1-phenyl-propan-1-one 
• 101-39-3 2-methyl-3-phenyl-2-propenal 
• 62-53-3 aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 612-58-8 3-methylquinoline 
• 100-59-4 phenylmagnesium chloride 
• 673-32-5 1-Phenylprop-1-yne 
• 271-58-9 anthranil 
• 35740-86-4 2-bromo-3-methylquinoline 
• 98-80-6 phenylboronic acid 
• 5344-90-1 2-Aminobenzyl alcohol 

Downstream Products

• 133348-05-7 2-phenylquinoline-3-carboxylic acid 
• 53779-50-3 1,3-dimethyl-2-phenyl-quinolinium; iodide 
• 14300-19-7 3-methyl-2-phenylquinoline N-oxide 
• 6829-11-4 3,4-dimethyl-2-phenylquinoline 
• 24005-26-3 3-methyl-2-phenyl-1,2,3,4-tetrahydroquinoline 

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.

NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines

Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.

Kinetic Resolution of 2,2-Disubstituted Dihydroquinolines through Chiral Phosphoric Acid-Catalyzed C6-Selective Asymmetric Halogenations

A novel kinetic resolution of 2,2-disubstituted dihydroquinolines was achieved by regioselective asymmetric halogenations enabled by chiral phosphoric acid catalysis. A series of dihydroquinolines bearing 2,2-disubstitutions were well-tolerated in these reactions, generating both the recovered dihydroquinolines and C-6-brominated products with high enantioselectivities, with s-factors up to 149. In addition, this kinetic resolution protocol is also applicable for 2,2-disubstituted tetrahydroquinoline and asymmetric iodonation reaction.