369655-84-5

Basic information

• Product Name: 8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI)
• Synonyms: 8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI);8-quinoline,5,6,7,8-tetrhydro-,(8R)-;8-Quinolinamine, 5,6,7,8-tetrahydro-, (8R)-;(8R)-5,6,7,8-Tetrahydro-8-quinolinamine;(R)-(-)-8-Amino-5,6,7,8-tetrahydroquinoline;(R)-5,6,7,8-tetrahydroquinolin-8-aMine;(R)-5,6,7,8-tetrahydroquinolin-8-aMine hydrochloride;(R)-5,6,7,8-Tetrahydro-quinolin-8-ylamine
• CAS NO: 369655-84-5
• Molecular Formula: C9H12N2
• Molecular Weight: 148.21
• Product Categories: PYRIDINE;AMINEPRIMARY;Quinoline Derivertives;Heterocycle-other series
• Mol File: 369655-84-5.mol

Chemical Properties

• Boiling Point: 277.3 °C at 760 mmHg
• Flash Point: 146 °C
• Appearance: /
• Density: 1.081
• Vapor Pressure: 0.00456mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.93±0.20(Predicted)
• CAS DataBase Reference: 8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI)(369655-84-5)
• EPA Substance Registry System: 8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI)(369655-84-5)

Safety Data

• Hazardous Substances Data: 369655-84-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI) is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and chirality allow for the development of enantioselective drugs, which can exhibit improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Agrochemical Development:
In the agrochemical industry, 8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI) serves as a crucial component in the synthesis of bioactive compounds. Its incorporation into agrochemicals can lead to the development of more effective and targeted pest control agents, contributing to sustainable agricultural practices.
Used in Organic Chemistry Research:
8-Quinolinamine,5,6,7,8-tetrahydro-,(8R)-(9CI) is employed as a versatile building block in organic chemistry research. Its reactivity and structural features make it suitable for a wide range of chemical transformations, enabling the synthesis of novel compounds with potential applications in various fields.

InChI:InChI=1/C9H12N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h2,4,6,8H,1,3,5,10H2/t8-/m1/s1

Upstream product

• 14631-46-0 5,6,7,8-tetrahydroquinoline-8-ol 
• 298181-83-6 5,6,7,8-tetrahydroquinolin-8-yl amine 
• 502612-35-3 (R)-N-(5,6,7,8-tetrahydroquinolin-8-yl)acetamide 

Downstream Products

• 298181-83-6 5,6,7,8-tetrahydroquinolin-8-yl amine 

Relevant articles and documents

Spontaneous enzymatically mediated dynamic kinetic resolution of 8-amino-5,6,7,8-tetrahydroquinoline

A spontaneous dynamic kinetic resolution of 8-amino-5,6,7,8- tetrahydroquinoline 1 was observed in the presence of Candida antarctica Lipase B, in which a >60% yield of (R)-acetamide [(R)-2] was isolated from the racemic amine. The spontaneous formation of ketone 3, followed by a condensation/hydrolysis sequence with the remaining (S)-amine 1, via enamine 4, provides the necessary racemization pathway.

Monofunctional PtII Complexes Based on 8-Aminoquinoline: Synthesis and Pharmacological Characterization

Among the heterocyclic compounds, 8-aminoquinoline and its derivatives have become important candidates for the preparation of new antiproliferative metallo-drugs. Here, we reported the synthesis and cytotoxicity evaluation of a series of platinum complexes using 8-aminoquinoline and its chiral 5,6,7,8-tetrahydro-derivatives as chelating ligands. In the proposed complexes, a differently and opportunely alkylated imidazole was used to prepare the corresponding monofunctional platinum complexes. The preliminary cytotoxicity evaluation was carried out on the highly aggressive MDA-MB-231, invasive and poorly differentiated triple-negative breast cancer (TNBC) cell line, furnishing a significant IC50 10.9 ± 1.3 μM for Pt-IV. This series of complexes revealed an induction of p53, interfering with the progression of the G0/G1 phase of the cell cycle.

Synthesis of enantiomerically pure amino-substituted fused bicyclic rings

This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.

Enzymatic resolution of bicyclic 1-heteroarylamines using Candida antarctica lipase B

Candida antarctica lipase B has been used to kinetically resolve a structurally diverse series of bicyclic 1-heteroaryl primary amines by enantioselective acetylation. High yields of either enantiomer could be obtained with excellent enantioselectivity (90-99% ee), while the undesired enantiomer could, in some cases, be recycled by thermal racemization. The absolute stereochemistry of the products was confirmed by an X-ray crystal structure.