27356-46-3

Usage

Uses

Used in Dye Production:
6-Methyl-2-phenyl-quinoline is utilized as an intermediate in the synthesis of dyes, contributing to the creation of a diverse range of colorants for various applications.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 6-methyl-2-phenyl-quinoline serves as a key component in the development of new drugs, potentially enhancing the therapeutic options available for treating various health conditions.
Used in Organic Compounds Synthesis:
6-methyl-2-phenyl-quinoline is employed as a building block in the synthesis of other organic compounds, expanding the scope of chemical research and innovation.
Used in Fluorescence and Chemiluminescence Research:
6-Methyl-2-phenyl-quinoline is applied in the field of fluorescence and chemiluminescence, where its properties are harnessed for analytical and diagnostic purposes, contributing to advancements in scientific understanding and technology.
Used in Anticancer Research:
6-Methyl-2-phenyl-quinoline is explored as a potential anticancer agent, with ongoing studies aiming to uncover its biological activities and therapeutic potential against cancer cells, offering hope for the development of novel cancer treatments.

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

Upstream product

• 4053-42-3 6-methylquinoline-N-oxide 
• 100-52-7 benzaldehyde 
• 106-49-0 p-toluidine 
• 74-86-2 acetylene 
• 64-17-5 ethanol 
• 33603-87-1 (Z)-3-chloro-3-phenyl-2-propenal 
• 91-62-3 6-methylquinoline 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 2272-45-9 benzal-p-toluidine 
• 2235-00-9 vinylcaprolactam 
• 107734-14-5 4-methyl-2-vinylaniline 
• 34897-84-2 2-amino-5-methylbenzyl alcohol 
• 98-86-2 acetophenone 
• 583-68-6 2-bromo-p-toluidine 

Downstream Products

• 50971-40-9 2-phenyl-quinoline-6-carboxylic acid 
• 36910-41-5 7-methyl-2,4,4-triphenyl-1,2,4,5-tetrahydro-2,5-methano-benzo[d][1,3]oxazepine 
• 50971-16-9 2-phenyl-6-bromomethyl-quinoline 
• 14300-20-0 6-methyl-2-phenylquinoline 1-oxide 

Relevant academic research and scientific papers

Mild and simple access to diverse 4-amino-substituted 2-phenyl-1,2,3,4- tetrahydroquinolines and 2-phenylquinolines based on a multicomponent imino diels-alder reaction

A straightforward synthesis of new 1-(2-phenyl-1,2,3,4-tetrahydroquinolin- 4-yl) pyrrolidin-2-ones/azepan-2-one from N-vinyl caprolactam/N-vinylpyrrolidin- 2-one and N-benzylideneaniline via the imino Diels-Alder reaction has been reported for the first time. Antimony(III) chloride has been shown to effectively catalyze imino-Diels-Alder reaction to afford both 2-phenylquinoline and 2-phenyl-1,2,3,4-tetrahydroquinolin derivatives in excellent yields at ambient temperature. The cis diastereoselectivity to give cis 2-phenyl-1,2,3,4-tetrahydroquinolines is also highlighted in this reaction. Copyrigh

Molybdatophosphoric acid/NaNO2/wet SiO2 as an efficient system for the aromatization of 1,2-dihydroquinolines under mild and heterogeneous conditions

A combination of molybdatophosphoric acid and NaNO2 in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of 1,2-dihydroquinolines to their corresponding quinoline derivatives in dichlomethane at room temperature with excellent yields. Copyright Taylor & Francis Group, LLC.

Rhodium-Catalyzed Dehydrogenative Annulation of N-Arylmethanimines with Vinylene Carbonate for Synthesizing Quinolines

Here we report a novel Rh-catalyzed C-H/C-H alkenylation of N-arylmethanimines with vinylene carbonate acting as a vinylene unit. Forty examples of C3,C4-nonsubstituted quinolines were achieved from commercially available starting materials. This identified process features an exceedingly simple system, a lower loading of catalyst, and the capacity for postfunctionalization with bioactive molecules.

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.

Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines

A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.

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.

Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt

A ruthenium complex bearing a functional 2,2′-bibenzimidazole ligand [(p-cymene)Ru(BiBzImH2)Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically active molecular was also undertaken. Notably, this research exhibits new potential of metal–ligand bifuctional catalysts for acceptorless dehydrogenative reactions.

Visible-light-induced photoxidation-Povarov cascade reaction: synthesis of 2-arylquinoline through alcohol andN-benzylanilines under mild conditionsviaAg/g-C3N4nanometric semiconductor catalyst

With a Ag/g-C3N4nanometric semiconductor as the photocatalyst, 2-arylquinolines were synthesized through a photoxidation-Povarov cascade reaction ofN-benzylanilines and alcohols under visible light irradiation. Under the blue light of a 3 W LED, good yields were achieved for various substrates in oxygen at room temperature. This methodology provides a green and mild alternative for the formation of 2-arylquinoline derivatives. Remarkably, the Ag/g-C3N4nanocomposite can be conveniently recovered and reused several times with satisfying yields.

The synthesis of quinolines: via denitrogenative palladium-catalyzed cascade reaction of o -aminocinnamonitriles with arylhydrazines

The first example of the palladium-catalyzed cascade reaction of o-aminocinnamonitriles with arylhydrazines has been achieved, providing an efficient synthetic pathway to access quinolines with moderate to good yields. Preliminary mechanistic experiments

Sustainable synthesis of quinolines (pyridines) catalyzed by a cheap metal Mn(I)-NN complex catalyst

This study represents the first example of a bidentate phosphine-free manganese(I)-NN complex catalyst for the synthesis of quinolines (pyridines) through acceptorless dehydrogenative condensation of various secondary alcohols with amino alcohols. The coupling reactions occurred at 3 mol% catalyst loading and 110°C, and tolerated diverse functional groups. Moderate to excellent yields ranging from 45% to 89% were achieved after 12 hr of reaction. The present protocol provides a concise and environmentally friendly method for the construction of heterocyclic compounds.