4501-08-0

Basic information

• Product Name: 6-phenyl-1,2,3,4-tetrahydroquinoline
• Synonyms: 6-phenyl-1,2,3,4-tetrahydroquinoline
• CAS NO: 4501-08-0
• Molecular Weight: 209.291
• Mol File: 4501-08-0.mol

Chemical Properties

• CAS DataBase Reference: 6-phenyl-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-phenyl-1,2,3,4-tetrahydroquinoline(4501-08-0)
• EPA Substance Registry System: 6-phenyl-1,2,3,4-tetrahydroquinoline(4501-08-0)

Safety Data

• Hazardous Substances Data: 4501-08-0(Hazardous Substances Data)

Upstream product

• 4501-11-5 N¹,N³-bis[(1,1'-biphenyl)-4-yl]propane-1,3-diamine 
• 5825-45-6 1-amino-1,2,3,4-tetrahydroquinoline 
• 71-43-2 benzene 
• 5332-25-2 6-bromoquinoline 
• 98-80-6 phenylboronic acid 
• 612-95-3 6-phenylquinoline 
• 91718-20-6 3-iodo-4-methoxy-1,1′-biphenyl 
• 1046152-59-3 4-amino-3-hydroxymethylbiphenyl 
• 64-17-5 ethanol 
• 22190-35-8 6-bromo-1,2,3,4-tetrahydroquinoline 

Downstream Products

• 4501-09-1 1-benzoyl-6-phenyl-1,2,3,4-tetrahydro-quinoline 

Relevant articles and documents

Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics

We report the first examples of radical cation Smiles rearrangements. A series of aryloxy alkylamines underwent spontaneous reaction, with the amino group displacing theipso-alkoxy group through substitution, at ambient temperature and under photoactivation by visible light in the presence of an acridinium catalyst (5 mol%). The study was extended to 3-(2-methoxyphenyl)propan-1-amine derivatives, which lack an appropriateipsoleaving group. Here, efficient cyclisations resulted in displacement of the methoxy group and formation of tetrahydroquinolines.

Synthesis of aryl-substituted quinolines and tetrahydroquinolines through Suzuki–Miyaura coupling reactions

The synthesis and characterization of substituted (trifluoromethoxy, thiomethyl, and methoxy) phenyl quinolines is described. Dichlorobis(triphenylphosphine)palladium(II)-catalyzed Suzuki–Miyaura cross-coupling of 6-bromo- and 6,8-dibromo-1,2,3,4-tetrahyd

Biological activity and molecular docking studies of some new quinolines as potent anticancer agents

Abstract: The objective of this study is to investigate the antiproliferative and cytotoxic properties and the?action mechanism of substituted quinoline and tetrahydroquinolines 3, 4, 5, 7, and 8 against rat glioblastoma (C6), human cervical cancer (HeLa), human adenocarcinoma (HT29) cancer cell lines by BrdU Cell Proliferation ELISA, Lactate Dehydrogenase, DNA laddering and Topoisomerase I assays. The results of the study showed that 6,8-dibromotetrahydroquinoline 3 possess in vitro antiproliferative activity against C6, HeLa, and HT29 cell lines while morpholine/piperazine substituted quinoline 7 and 8 showed selective antiproliferative activity on C6 cell line with IC50 values 47.5 and 46.3?μg/mL, respectively. Moreover, 6,8-dibromoTHQ 3 caused DNA fragmentation while it did not inhibit the Topoisomerase I (Topo I) enzyme. On the other hand, compound?8 did not cause DNA laddering while 8 inhibited the Topo I enzyme. According to these results, 6,8-dibromoTHQ 3 stimulates apoptosis on the C6 cell line while 6,8-dibromo-3-morhonilylquinoline (8) inhibits the Topo I enzyme to cause antiproliferative activity. Graphic abstract: [Figure not available: see fulltext.].

Ni0/Niδ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C-C and C-N Bonds

Simultaneous formation of C-C/C-N bonds provides insight into the bottom-up synthesis of N-heterocycles. This work reports Ni0/Niδ+ synergistic catalysis on the surface of Ni nanoparticles for the highly efficient one-pot formation of C-C/C-N bonds, affording 1,2,3,4-tetrahydroquinoline and its derivatives from 2-amino benzyl alcohol and ethanol without any addition of liquor base or external hydrogen. Ni0/Niδ+ synergistic catalysis has been achieved by regulating the Ni particle size or activating the Ni surface with O2. In the dehydrogenation of -CH2-OH to -CH=O, the formation of C==C and C=N bonds via concurrent cross-condensation, and the transformation of C=C/C=N to C-C/C-N via hydrogen transfer, ethanol dehydrogenation has been found to be the rate-determining step. Reducing the Ni particle size effectively increases the number of surface Niδ+ sites, which accelerates catalytic dehydrogenation through synergistic catalysis between surface Niδ+ and Ni0 sites. The number of surface Niδ+ sites can be further increased by appropriately activating the Ni surface with O2

Chemoselective One-Pot Synthesis of Functionalized Amino-azaheterocycles Enabled by COware

Functionalized bicyclic amino-azaheterocycles are rapidly accessed in a one-pot cross-coupling/reduction sequence enabled by the use of COware. Incompatible reagents are physically separated in a single reaction vessel to effect two chemoselective transformations - Suzuki-Miyaura cross-coupling and heteroarene reduction. The developed method allows access to novel heterocyclic templates, including semisaturated Hedgehog and dual PI3K/mTOR inhibitors, which show enhanced physicochemical properties compared to their unsaturated counterparts.

A TRIFLUOROMETHANESULFONIC ACID-CATALYZED REACTION OF ARYLHYDRAZINES WITH BENZENE

Arylhydrazines reacted with benzene in the presence of trifluoromethanesulfonic acid (TFSA) to give aminobiphenyls.This is a general method for the synthesis of aminobiphenyls.