101583-63-5

Basic information

• Product Name: 2-(2-phenylethyl)-1,2,3,4-tetrahydroquinoline
• Synonyms: 2-(2-phenylethyl)-1,2,3,4-tetrahydroquinoline
• CAS NO: 101583-63-5
• Molecular Weight: 237.345
• Mol File: 101583-63-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2-(2-phenylethyl)-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-phenylethyl)-1,2,3,4-tetrahydroquinoline(101583-63-5)
• EPA Substance Registry System: 2-(2-phenylethyl)-1,2,3,4-tetrahydroquinoline(101583-63-5)

Safety Data

• Hazardous Substances Data: 101583-63-5(Hazardous Substances Data)

Upstream product

• 4945-26-0 2-styrylquinoline 
• 1613-41-8 2-phenethyl-quinoline 
• 38101-69-8 2-[(E)-styryl]quinoline 
• 100-42-5 styrene 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 91-63-4 2-methylquinoline 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 53931-59-2 5-phenyl-1-penten-3-one 
• 2785-29-7 benzyl potassium 

Relevant articles and documents

Heterogeneous gold-catalyzed selective reductive transformation of quinolines with formic acid

Single phase rutile titania supported gold nanoparticles (Au/TiO2-R) are found to be efficient and versatile catalysts for chemo- and regioselective transfer hydrogenation of quinoline derivatives to 1,2,3,4-tetrahydroquinolines (THQs) using formic acid (FA) as a safe and convenient hydrogen source under mild conditions. The activity and chemoselectivity of the Au/TiO2-R catalyst towards THQs is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Furthermore, a straightforward and selective route to N-formyltetrahydroquinolines (FTHQ) directly from quinoline compounds and FA by one-pot, gold-catalyzed reductive N-formylation protocol is also established.

An efficient catalytic system for the hydrogenation of quinolines

A new catalytic system ([Ru(p-cymene)Cl2]2/I2) has been developed for the hydrogenation of quinoline derivatives with high reactivity. For the 2-methyl-quinoline, the hydrogenation reaction can proceed smoothly at an S/C of 20,000/1 with complete conversion. The iodine additive is important for the reactivity.

Boric acid catalyzed chemoselective reduction of quinolines

Boric acid promoted transfer hydrogenation of substituted quinolines to synthetically versatile 1,2,3,4-tetrahydroquinolines (1,2,3,4-THQs) was described under mild reaction conditions using a Hantzsch ester as a mild organic hydrogen source. This methodology is practical and efficient, where isolated yields are excellent and reducible functional groups are well tolerated in the N-heteroarene moiety. The reaction parameters and tentative mechanistic pathways are demonstrated by various control experiments and NMR studies. The present work can also be scaled up to obtain gram quantities and the utility of the developed process is illustrated by the transformation of 1,2,3,4-THQs into a series of biologically important molecules including the antiarrhythmic drug nicainoprol.

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.