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
• Article Data: 19

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

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

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.

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.