14631-48-2

Basic information

• Product Name: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE
• Synonyms: 2,3-CYCLOHEXENOPYRIDINE-N-OXIDE;5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE;5,6,7,8-TETRAHYDROQUINOLINE 1-OXIDE;1-oxido-5,6,7,8-tetrahydroquinolin-1-ium
• CAS NO: 14631-48-2
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• Mol File: 14631-48-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 69 °C
• Boiling Point: 358°C at 760 mmHg
• Flash Point: 170.3°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 5.42E-05mmHg at 25°C
• Refractive Index: 1.597
• PKA: 1.35±0.20(Predicted)
• CAS DataBase Reference: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE(14631-48-2)
• EPA Substance Registry System: 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE(14631-48-2)

Safety Data

• Hazardous Substances Data: 14631-48-2(Hazardous Substances Data)

Usage

General Description

5,6,7,8-Tetrahydro-1-quinoliniumolate is a chemical compound with the molecular formula C9H11NO. It is a quinoline derivative that contains a quaternary nitrogen atom, making it a quaternary ammonium salt. This chemical compound is commonly used in organic synthesis and as a reagent in chemical reactions. It has been studied for its potential applications in pharmaceuticals, with research suggesting it may have anticancer and neuroprotective properties. 5,6,7,8-TETRAHYDRO-1-QUINOLINIUMOLATE is also of interest in the field of materials science, particularly in the development of new functional materials.

InChI:InChI=1/C9H11NO/c11-10-7-3-5-8-4-1-2-6-9(8)10/h3,5,7H,1-2,4,6H2

Upstream product

• 10500-57-9 5,6,7,8-tetrahydroquinoline 

Downstream Products

• 134220-57-8 (3aS,3bR,9aR,10aR)-5-(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-2-phenyl-3a,3b,5,6,7,8,9a,10a-octahydro-10-oxa-2,4-diaza-pentaleno[1,2-b]naphthalene-1,3-dione 
• 125162-98-3 4-Nitro-5,6,7,8-tetrahydroquinoline N-oxide 
• 150459-78-2 5,6,7,8,-tetrahydroquinoline-2-carbonitrile 
• 106057-23-2 8-chloro-5,6,7,8-tetrahydroquinoline 
• 14631-46-0 5,6,7,8-tetrahydroquinoline-8-ol 
• 912277-32-8 (R)-5,6,7,8-tetrahydroquinolin-8-yl dicyclohexylphosphinite 
• 451466-81-2 (R)-8-hydroxy-5,6,7,8-tetrahydroquinoline 
• 14631-47-1 5,6,7,8-tetrahydroquinolin-8-yl acetate 
• 1260435-69-5 (8R)-5,6,7,8-tetrahydro-8-quinolinyl (2S)-3,3,-trifluoro-2-(methyloxy)-2-phenylpropanoate 
• 1260435-66-2 (8S)-5,6,7,8-tetrahydro-8-quinolinyl (2S)-3,3,-trifluoro-2-(methyloxy)-2-phenylpropanoate 
• 1417437-47-8 2-cyclohexyl-5,6,7,8-tetrahydroquinoline 1-oxide 
• 92850-39-0 2-phenyl-5,6,7,8-tetrahydroquinoline N-oxide 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 
• 56826-69-8 5,6,7,8-tetrahydro-8-quinolinone 

Relevant articles and documents

Water-soluble inhibitors of ABCG2 (BCRP) – A fragment-based and computational approach

A good balance between hydrophilicity and lipophilicity is a prerequisite for all bioactive compounds. If the hydrophilicity of a compound is low, its solubility in water will be meager. Many drug development failures have been attributed to poor aqueous solubility. ABCG2 inhibitors are especially prone to be insoluble since they have to address the extremely large and hydrophobic multidrug binding site in ABCG2. For instance, our previous, tariquidar-related ABCG2 inhibitor UR-MB108 (1) showed high potency (79 nM), but very low aqueous solubility (78 nM). To discover novel potent ABCG2 inhibitors with improved solubility we pursued a fragment-based approach. Substructures of 1 were optimized and the fragments ‘enlarged’ to obtain inhibitors, supported by molecular docking studies. Synthesis was achieved, i.a., via Sonogashira coupling, click chemistry and amide coupling. A kinetic solubility assay revealed that 1 and most novel inhibitors did not precipitate during the short time period of the applied biological assays. The solubility of the compounds in aqueous media at equilibrium was investigated in a thermodynamic solubility assay, where UR-Ant116 (40), UR-Ant121 (41), UR-Ant131 (48) and UR-Ant132 (49) excelled with solubilities between 1 μM and 1.5 μM – an up to 19-fold improvement compared to 1. Moreover, these novel N-phenyl-chromone-2-carboxamides inhibited ABCG2 in a Hoechst 33342 transport assay with potencies in the low three-digit nanomolar range, reversed MDR in cancer cells, were non-toxic and proved stable in blood plasma. All properties make them attractive candidates for in vitro assays requiring long-term incubation and in vivo studies, both needing sufficient solubility at equilibrium. 41 and 49 were highly ABCG2-selective, a precondition for developing PET tracers. The triple ABCB1/C1/G2 inhibitor 40 qualifies for potential therapeutic applications, given the concerted role of the three transporter subtypes at many tissue barriers, e.g. the BBB.

Efficient Pyrazolo[5,4-f]quinoxaline Functionalized Os(II) Based Emitter with an Electroluminescence Peak Maximum at 811 nm

Upon fusing the pyrazinyl pyrazole entity in giving pyrazolo[3,4-f]quinoxaline chelate, the corresponding Os(II) based NIR emitter exhibited “invisible” and efficient electroluminescence with a peak maximum at 811 nm. A maximum external quantum efficiency

Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides

A photoredox catalytic method has been developed for the direct C2 alkylation of pyridine N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2-alkylated pyridine N-oxides under mild conditions. Mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.