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
• Article Data: 6

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

• 5825-45-6 1-amino-1,2,3,4-tetrahydroquinoline 
• 71-43-2 benzene 
• 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 
• 98-80-6 phenylboronic acid 
• 612-95-3 6-phenylquinoline 
• 5332-25-2 6-bromoquinoline 
• 4501-11-5 N¹,N³-bis[(1,1'-biphenyl)-4-yl]propane-1,3-diamine 

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.

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.].

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.