123612-59-9

Basic information

• Product Name: 1,2,3,4-tetrahydro-2-(4-methylphenyl)quinoline
• Synonyms: 1,2,3,4-tetrahydro-2-(4-methylphenyl)quinoline
• CAS NO: 123612-59-9
• Molecular Weight: 223.318
• Mol File: 123612-59-9.mol

Chemical Properties

• CAS DataBase Reference: 1,2,3,4-tetrahydro-2-(4-methylphenyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-tetrahydro-2-(4-methylphenyl)quinoline(123612-59-9)
• EPA Substance Registry System: 1,2,3,4-tetrahydro-2-(4-methylphenyl)quinoline(123612-59-9)

Safety Data

• Hazardous Substances Data: 123612-59-9(Hazardous Substances Data)

Upstream product

• 24667-94-5 2-(4-methylphenyl)quinoline 
• 2417-95-0 p-tolyllithium 
• 5720-05-8 4-methylphenylboronic acid 
• 612-62-4 2-Chloroquinoline 
• 579-71-5 2-nitrostyrene 
• 3333-13-9 p-allyltoluene 
• 5344-90-1 2-Aminobenzyl alcohol 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 2005-43-8 2-bromoquinoline 
• 122-00-9 para-methylacetophenone 
• 137265-96-4 N-(2,3-dihydro-1H-inden-1-yl)-O-methylhydroxylamine 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 91-22-5 quinoline 
• 123612-54-4 2-p-Tolyl-1,2-dihydro-quinoline 

Downstream Products

• 1016275-45-8 (S)-2-(4’-methylphenyl)-1,2,3,4-tetrahydroquinoline 
• 24667-94-5 2-(4-methylphenyl)quinoline 

Relevant articles and documents

Cyclopentadiene-based Br?nsted acid as a new generation of organocatalyst for transfer hydrogenation of 2-substituted quinoline derivatives

A simple and readily available cyclopentadiene-based Br?nsted acid was employed to catalyze the transfer hydrogenation of 2-substituted quinolines using Hantzsch ester as the hydrogen source. This conceptually new designed organocatalyst demonstrates remarkably high efficiency for this transformation and a variety of substituted 1,2,3,4-tetrahydroquinoline derivatives were afforded in excellent yields under mild reaction conditions.

Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes

A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N -oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H 2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.

Efficient dehydrogenation of 1,2,3,4-tetrahydroquinolines mediated by dialkyl azodicarboxylates

Various dialkyl azodicarboxylates were investigated for the dehydrogenation of 1,2,3,4-tetrahydroquinolines to quinolines. The dehydrogenation rates varied according to the electronic and steric nature of the used dialkyl azodicarboxylates. Among solvents screened with diethyl azodicarboxylate, chloroform exhibited superior results to others. A variety of 1,2,3,4-tetrahydroquinolines underwent the present dehydrogenation to produce the corresponding quinolines. Diethyl hydrazodicarboxylate, which is a reduced species of diethyl azodicarboxylate, was easily separated for recycle.

PREPARATION METHOD OF 2-SUBSTITUTED 1,2,3,4-TETRAHYDROQUINOLINE COMPOUND

2 -substituted quinoline compounds are disclosed. The present invention relates to a 2 -substituted 2 -tetrahydroquinoline compound by hydroconversion of 1, 2, 3, 4 -substituted quinoline compounds using a catalyst composition comprising an isothiuronium salt and a Handoesr. In accordance with the present invention, 2 -substituted 1, 2, 3, 4 -tetrahydroquinoline compounds can be produced in high yield with improved reaction efficiency and reaction rate.

S-Benzyl-N,N'-diphenyl substituted isothiouronium iodide as a highly efficient organocatalyst for transfer hydrogenation of 2-substituted quinolines

An isothiouronium organocatalyst prepared from thiourea was first employed to catalyze the transfer hydrogenation of various 2-alkyl and arylquinolines with Hantzsch ester as the hydrogen source. This metal-free catalyzed reduction of 2-substituted quinoline efficiently rendered good to excellent yields of tetrahydroquinolines under mild conditions with a small amount of catalyst (5 mol%).

Asymmetric Synthesis of Hydroquinolines with α,α-Disubstitution through Organocatalyzed Kinetic Resolution

The first kinetic resolution of hydroquinoline derivatives with α,α-disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate- and enantio-determining electrophilic attack promoted by a network of attractive non-covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N-heterocycles with α,α-disubstitution.

Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN3Pincer Catalyst

A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.

CONVERSION OF TETRAHYDROQUINOLINE DERIVATIVES TO QUINOLINE USING AZOCOMPOUND

The present invention relates to a method of converting tetrahydroquinoline derivatives into quinoline using an azo compound and, more specifically, to a conversion method which is performed in a deuterium chloroform (CDCl_3) or chloroform (CHCl_3) solution including dialkyl azodicarboxylate, which is a method of producing quinoline through a dehydrogenation reaction of 1,2,3,4-tetrahydroquinoline. According to the present invention, a dehydrogenation reaction rate is dependent on the electronic and steric properties of used dialkyl azodicarboxylate; and chloroform shows better results than other substances in solvents screened with diethyl azodicarboxylate. Various types of 1,2,3,4-tetrahydroquinoline undergo the dehydration reaction of the present invention to produce the corresponding quinoline in a yield of at least 90%; and diethyl hydrazo dicarboxylate, which is a reduced form of diethyl azodicarboxylate, is readily separated and recyclable.COPYRIGHT KIPO 2020

Silver-Catalyzed Reduction of Quinolines in Water

A ligand- and base-free silver-catalyzed reduction of quinolines and electron-deficient aromatic N-heteroarenes in water has been described. Mechanistic studies revealed that the effective reducing species was Ag-H. This versatile catalytic protocol provided facile, environmentally friendly, and practical access to a variety of 1,2,3,4-tetrahydroquinoline derivatives at room temperature.

Fluorobissulfonylmethyl Iodides: An Efficient Scaffold for Halogen Bonding Catalysts with an sp3-Hybridized Carbon-Iodine Moiety

The halogen-bond donors FBSM-I and FBDT-I, which contain an sp3-hybridized carbon-iodine (Csp3-I) moiety, were designed and synthesized. The highly electron-withdrawing nature of the fluorobissulfonyl-methane scaffold leads to the ge