612-95-3

Basic information

• Product Name: 6-phenylquinoline
• Synonyms: 6-phenylquinoline
• CAS NO: 612-95-3
• Molecular Formula: C₁₅H₁₁N
• Molecular Weight: 205.25454
• EINECS: 210-325-1
• Mol File: 612-95-3.mol
• Article Data: 37

Chemical Properties

• Melting Point: 115-116℃
• Boiling Point: 360℃
• Flash Point: 157℃
• Appearance: /
• Density: 1.127
• Vapor Pressure: 4.87E-05mmHg at 25°C
• Refractive Index: 1.6550 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-phenylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-phenylquinoline(612-95-3)
• EPA Substance Registry System: 6-phenylquinoline(612-95-3)

Safety Data

• Hazardous Substances Data: 612-95-3(Hazardous Substances Data)

Usage

Purification Methods

Crystallise 6-pKEst phenylquinoline from EtOH (charcoal). The picrate has m 105o (from Me2CO). It has UV with at 253nm max in aqueous EtOH and 263 and 325nm in aqueous HCl. [Beilstein 20 H 483, 20 III/IV 4151.]

InChI:InChI=1/C15H11N/c1-2-5-12(6-3-1)13-8-9-15-14(11-13)7-4-10-16-15/h1-11H

Upstream product

• 4075-79-0 4-phenylacetanilide 
• 56-81-5 glycerol 
• 76-86-8 Triphenylsilyl chloride 
• 426265-40-9 quinolin-6-yl 4-methylbenzene-1-sulfonate 
• 98-80-6 phenylboronic acid 
• 1092513-18-2 quinolin-6-yl methanesulfonate 
• 780-69-8 triethoxyphenylsilane 
• 612-57-7 6-chloroquinoline 
• 71-43-2 benzene 
• 5332-25-2 6-bromoquinoline 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 108-86-1 bromobenzene 
• 5344-90-1 2-Aminobenzyl alcohol 
• 98-86-2 acetophenone 

Downstream Products

• 29969-55-9 2-chloro-6-phenyl-quinoline 
• 1309784-41-5 C₂₂H₁₇N 
• 94878-29-2 2,6-diphenylquinoline 
• 91875-31-9 2-methyl-6-phenylquinoline 
• 4501-08-0 6-phenyl-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles

A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.

A Highly Efficient Monophosphine Ligand for Parts per Million Levels Pd-Catalyzed Suzuki–Miyaura Coupling of (Hetero)Aryl Chlorides

A new indolylphosphine WK-phos has been synthesized for Pd-catalyzed Suzuki–Miyaura coupling of (hetero)aryl chlorides with (alkyl)arylboronic acids. Comprising this newly developed ligand with palladium(II) acetate, the resulting catalyst system was found to be highly effective in facilitating the reaction even when the catalyst loading reaches parts per million levels (e.g. 10 ppm). These examples represent one of the lowest catalyst loadings reported to date of employing monophosphine (e.g. Ar-PCy2) for Suzuki–Miyaura reactions. The ligand geometry has also been well-characterized by single-crystal X-ray crystallography.

Double Hydroboration of Quinolines via Borane Catalysis: Diastereoselective One Pot Synthesis of 3-Hydroxytetrahydroquinolines

Described herein is an organoborane-catalysed consecutive borylative reduction of quinolines and isoquinolines to furnish tetrahydro(iso)quinolines bearing a C(sp3)?B bond β to the nitrogen atom. The installed C?B bond is oxidatively transformed to the hydroxy group in one pot. The present double hydroboration is proposed to proceed via a stepwise ionic mechanism involving a boronium ion. The stereo-outcome was found to be dependent on the position (C2 vs C4) of the substituents in quinolines. (Figure presented.).