137595-45-0

Basic information

• Product Name: Quinoline, 6-fluoro-3-phenyl-
• CAS NO: 137595-45-0
• Molecular Formula: C15H10FN
• Molecular Weight: 223.25
• Mol File: 137595-45-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Quinoline, 6-fluoro-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 6-fluoro-3-phenyl-(137595-45-0)
• EPA Substance Registry System: Quinoline, 6-fluoro-3-phenyl-(137595-45-0)

Safety Data

• Hazardous Substances Data: 137595-45-0(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 67-68-5 dimethyl sulfoxide 
• 371-40-4 4-fluoroaniline 
• 748805-85-8 (2-amino-5-fluorophenyl)methanol 
• 122-78-1 phenylacetaldehyde 
• 536-74-3 phenylacetylene 
• 96-09-3 styrene oxide 
• 60144-53-8 N-(tert-butoxycarbonyl)-4-fluoroaniline 
• 7089-34-1 ((Z)-3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate 

Relevant articles and documents

[3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO

A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH?) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (═CH?) to the pyridine ring in quinoline molecules. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields. On the basis of the control experiments and the literature, a plausible mechanism is proposed.

Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines

An unexpected annulation among 2-aminobenzyl alcohols, benzaldehydes, and DMSO to quinolines has been disclosed. For the reported annulation between 2-aminobenzyl alcohols and benzaldehydes, the change of the solvent from toluene to DMSO led to the change of the product from the diheteroatomic cyclic benzoxazines to monoheteroatomic cyclic quinolines. This annulation can be used to synthesize regioselectively different substituted quinolines by the choice of different 2-amino alcohols, aldehydes, and sulfoxides as substrates. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines. On the basis of the control experiments and literatures, a plausible mechanism for this annulation was proposed.

Copper-Catalyzed Ring-Opening/Reconstruction of Anthranils with Oxo-Compounds: Synthesis of Quinoline Derivatives

A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.