1721-91-1

Basic information

• Product Name: Quinoline, 2-methyl-3-phenyl-
• CAS NO: 1721-91-1
• Molecular Formula: C16H13N
• Molecular Weight: 219.286
• Mol File: 1721-91-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Quinoline, 2-methyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 2-methyl-3-phenyl-(1721-91-1)
• EPA Substance Registry System: Quinoline, 2-methyl-3-phenyl-(1721-91-1)

Safety Data

• Hazardous Substances Data: 1721-91-1(Hazardous Substances Data)

Upstream product

• 552-89-6 2-nitro-benzaldehyde 
• 95-20-5 2-methyl-1H-indole 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 5344-90-1 2-Aminobenzyl alcohol 
• 103-79-7 1-phenyl-acetone 
• 673-32-5 1-Phenylprop-1-yne 
• 506437-31-6 C₂₀H₂₄N₂ 
• 91-56-5 indole-2,3-dione 
• 72844-84-9 N-{2-[(E)-2-phenylethenyl]phenyl}acetamide 
• 614-76-6 N-acetyl-2-bromoaniline 
• 529-23-7 o-aminobenzaldehyde 
• 72844-88-3 o-trans-Styrylthioacetanilide 
• 6319-87-5 2-methyl-3-phenylquinoline-4-carboxylic acid 

Downstream Products

• 1400975-27-0 1-methyl-4-phenylpyrrolo[1,2-a]quinoline 
• 1415584-35-8 3-phenyl-2-vinylquinoline 
• 412323-06-9 (3-phenyl-[2]quinolyl)-pyruvic acid ethyl ester 

Relevant articles and documents

Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines

Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing α-chlorodiazirines as thermal precursors to the corresponding chlorocarbenes, the traditional haloform-based protocol central to the parent Ciamician-Dennstedt rearrangement can be modified to directly afford 3-(hetero)arylpyridines and quinolines. Chlorodiazirines are conveniently prepared in a single step by oxidation of commercially available amidinium salts. Selectivity as a function of pyrrole substitution pattern was examined, and a predictive model based on steric effects is put forward, with DFT calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is further demonstrated through the preparation of quinolinophanes and the skeletal editing of pharmaceutically relevant pyrroles.

Metal- and Protection-Free [4 + 2] Cycloadditions of Alkynes with Azadienes: Assembly of Functionalized Quinolines

A base promoted, protection-free, and regioselective synthesis of highly functionalized quinolines via [4 + 2] cycloaddition of azadienes (generated in situ from o-aminobenzyl alcohol) with internal alkynes has been discovered. The reaction tolerates a wide variety of functional groups which has been successfully extended with diynes, (2-aminopyridin-3-yl)methanol, and 1,4-bis(phenylethynyl)benzene to afford (Z)-phenyl-2-styrylquinolines, phenylnaphthyridine, and alkyne-substituted quinolines, respectively. The proposed mechanism and significant role of the solvent were well supported by isolating the azadiene intermediate and deuterium-labeling studies.

Addition of arylboronic acids to arylpropargyl alcohols en route to indenes and quinolines

A regio- and stereoselective rhodium-catalyzed synthesis of trisubstituted allylic alcohols is described. The utility of these synthons is demonstrated in a convenient synthesis of indenes and quinolines.