4789-76-8

Usage

Uses

Used in Organic Synthesis:
4-methyl-2-phenyl-quinoline is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block in the creation of new molecules with potential applications in various industries.
Used in Pharmaceutical Production:
As a precursor, 4-methyl-2-phenyl-quinoline is used in the production of pharmaceuticals. Its presence in the synthesis process contributes to the development of new drugs with potential therapeutic benefits.
Used in Dye Manufacturing:
This quinoline derivative is also used in the manufacturing of dyes, where its yellow color and chemical properties are harnessed to create a range of colorants for various applications.
Used in Fluorescent Probe Development:
4-methyl-2-phenyl-quinoline is utilized as a fluorescent probe in biological and chemical research. Its fluorescent properties allow it to be used in imaging and detection techniques, providing valuable insights into various scientific studies.
Used in Anti-Cancer Research:
4-methyl-2-phenyl-quinoline has been studied for its potential as an anti-cancer agent. Its biological properties are being investigated for their ability to target and treat cancer cells, offering a promising avenue for the development of new cancer therapies.
Used in Heterocyclic Compound Synthesis:
4-methyl-2-phenyl-quinoline serves as a building block in the synthesis of heterocyclic compounds, which have potential applications in medicine and materials science. Its role in creating these complex molecules contributes to the advancement of various fields, including drug discovery and material development.

InChI:InChI=1/C16H13N/c1-12-11-16(13-7-3-2-4-8-13)17-15-10-6-5-9-14(12)15/h2-11H,1H3

Upstream product

• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 551-93-9 2-aminoacetophenone 
• 98-86-2 acetophenone 
• 94-36-0 dibenzoyl peroxide 
• 634-47-9 2-chloro-4-methylquinoline 
• 98-80-6 phenylboronic acid 
• 29268-33-5 4-hydroxymethyl-2-phenylquinoline 
• 4053-40-1 4-methylquinoline 1-oxide 
• 98-85-1 1-Phenylethanol 
• 13361-64-3 trimethyl(propargyl)silane 
• 1750-36-3 (E)-N-benzylidenebenzenamine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 78450-59-6 1,1,1-trichloro-3-(2-phenyl-[4]quinolyl)-propan-2-ol 
• 117839-38-0 2-phenyl-4-quinolinecarboxaldehyde 
• 3475-16-9 4-methyl-2-phenylquinoline 1-oxide 
• 332124-42-2 3-(2-phenyl-4-quinolinyl)benzoic acid ethyl ester 
• 14365-89-0 4-(4-methyl-quinolin-2-yl)-phenol 
• 580-38-1 4-(4-methyl-[2]quinolyl)-aniline 
• 47492-97-7 N,N-diethyl-N'-(2-phenyl-[4]quinolylmethyl)-propanediyldiamine 
• 14365-92-5 4-methyl-2-(4-nitrophenyl)quinoline 

Relevant academic research and scientific papers

Highly efficient and spectrally stable white organic light-emitting diodes using new red heteroleptic Iridium(III) complexes

Highly efficient red phosphorescent iridium(III) complexes, (MPQ)2Ir(Pppy) and (MPQ)2Ir(TMSppy) based on 4-methyl-2-phenylquinoline (MPQ) as a cyclometalated main ligand and 2-[(1,1′-biphenyl)4-yl]pyridine (Pppy) or 2-[4-(trimethylsi

Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines

Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.

Cobalt-catalyzed cross-coupling of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium reagents

Cobalt-catalyzed cross-couplings of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium halides proceeded efficiently with the aid of cobalt(II) catalyst and copper(I) salt in tetrahydrofuran at ambient temperature, producing the desired

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.

Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines

Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).

Novel anti-solvent quenching near-infrared two-zone dye and preparation method thereof Preparation method and application thereof

The invention provides a novel anti-solvent quenching near-infrared two-zone dye and a preparation method and application thereof, and relates to a novel anti-solvent quenching NIR-II dye containing a nitrogen heterocyclic ring. Experiments show that the

Magnetite (Fe3O4) nanoparticles-supported dodecylbenzenesulfonic acid as a highly efficient and green heterogeneous catalyst for the synthesis of substituted quinolines and 1-amidoalkyl-2-naphthol derivatives

Abstract: Magnetically retrievable, magnetite (Fe3O4) nanoparticles-supported dodecylbenzenesulfonic acid (DDBSA@MNP) was synthesized and characterized through different analytical techniques such as TEM, XRD, FTIR, TGA, SEM, EDX and

[(PPh3)2NiCl2]-Catalyzed C-N bond formation reaction via borrowing hydrogen strategy: Access to diverse secondary amines and quinolines

Commercially available [(PPh3)2NiCl2] was found to be an efficient catalyst for the mono-N-alkylation of (hetero)- A romatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine (5b) and mepyramine (5c), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy is also successful in accessing various quinoline derivatives following the acceptorless dehydrogenation pathway.

Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes

The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.

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.