560085-09-8

Basic information

• Product Name: Quinoline, 7-fluoro-1,2,3,4-tetrahydro-2-methyl- (9CI)
• Synonyms: 7-Fluoro-2-Methyl-1,2,3,4-tetrahydro-quinoline;Quinoline, 7-fluoro-1,2,3,4-tetrahydro-2-methyl- (9CI)
• CAS NO: 560085-09-8
• Molecular Formula: C10H12FN
• Molecular Weight: 165.2073832
• Product Categories: HALIDE
• Mol File: 560085-09-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Quinoline, 7-fluoro-1,2,3,4-tetrahydro-2-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 7-fluoro-1,2,3,4-tetrahydro-2-methyl- (9CI)(560085-09-8)
• EPA Substance Registry System: Quinoline, 7-fluoro-1,2,3,4-tetrahydro-2-methyl- (9CI)(560085-09-8)

Safety Data

• Hazardous Substances Data: 560085-09-8(Hazardous Substances Data)

Upstream product

• 1128-74-1 7-fluoro-2-methyl-quinoline 

Downstream Products

• 1190876-65-3 (S)-7-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 
• 1388106-07-7 C₁₀H₁₂FN 
• 1128-74-1 7-fluoro-2-methyl-quinoline 

Relevant articles and documents

The formation of all-cis-(multi)fluorinated piperidines by a dearomatization–hydrogenation process

Piperidines and fluorine substituents are both independently indispensable components in pharmaceuticals, agrochemicals and materials. Logically, the incorporation of fluorine atoms into piperidine scaffolds is therefore an area of tremendous potential. However, synthetic approaches towards the formation of these architectures are often impractical. The diastereoselective synthesis of substituted monofluorinated piperidines often requires substrates with pre-defined stereochemistry. That of multifluorinated piperidines is even more challenging, and often needs to be carried out in multistep syntheses. In this report, we describe a straightforward process for the one-pot rhodium-catalysed dearomatization–hydrogenation of fluoropyridine precursors. This strategy enables the formation of a plethora of substituted all-cis-(multi)fluorinated piperidines in a highly diastereoselective fashion through pyridine dearomatization followed by complete saturation of the resulting intermediates by hydrogenation. Fluorinated piperidines with defined axial/equatorial orientation of fluorine substituents were successfully applied in the preparation of commercial drugs analogues. Additionally, fluorinated PipPhos as well as fluorinated ionic liquids were obtained by this dearomatization–hydrogenation process.

Tuning the Catalytic Performance of Cobalt Nanoparticles by Tungsten Doping for Efficient and Selective Hydrogenation of Quinolines under Mild Conditions

Non-noble bimetallic CoW nanoparticles (NPs) partially embedded in a carbon matrix (CoW@C) have been prepared by a facile hydrothermal carbon-coating methodology followed by pyrolysis under an inert atmosphere. The bimetallic NPs, constituted by a multishell core-shell structure with a metallic Co core, a W-enriched shell involving Co7W6 alloyed structures, and small WO3 patches partially covering the surface of these NPs, have been established as excellent catalysts for the selective hydrogenation of quinolines to their corresponding 1,2,3,4-tetrahydroquinolines under mild conditions of pressure and temperature. It has been found that this bimetallic catalyst displays superior catalytic performance toward the formation of the target products than the monometallic Co@C, which can be attributed to the presence of the CoW alloyed structures.

General and Chemoselective Copper Oxide Catalysts for Hydrogenation Reactions

Copper oxide catalysts have been prepared by pyrolysis of copper acetate on aluminum oxide. The material resulting from pyrolysis at 800 °C allows for catalytic hydrogenations at low temperature of a variety of unsaturated compounds such as quinolines, alkynes, ketones, imines, and polycyclic aromatic hydrocarbons as well as nitroarenes with good activity and selectivity.

Nanolayered Cobalt-Molybdenum Sulfides as Highly Chemo- and Regioselective Catalysts for the Hydrogenation of Quinoline Derivatives

Herein, a general protocol for the preparation of a broad range of valuable N-heterocyclic products by hydrogenation of quinolines and related N-heteroarenes is described. Interestingly, the catalytic hydrogenation of the N-heteroarene ring is chemoselectively performed when other facile reducible functional groups, including alkenes, ketones, cyanides, carboxylic acids, esters, and amides, are present. The key to successful catalysis relies on the use of a nanolayered cobalt-molybdenum sulfide catalyst hydrothermally synthesized from earth-abundant metal precursors. This heterogeneous system displays a tunable composition of phases that allows for catalyst regeneration. Its catalytic activity depends on the composition of the mixed phase of cobalt sulfides, being higher with the presence of Co3S4, and could also be associated with the presence of transient Co-Mo-S structures that mainly vanish after the first catalytic run.

A robust iron catalyst for the selective hydrogenation of substituted (iso)quinolones

By applying N-doped carbon modified iron-based catalysts, the controlled hydrogenation of N-heteroarenes, especially (iso)quinolones, is achieved. Crucial for activity is the catalyst preparation by pyrolysis of a carbon-impregnated composite, obtained from iron(ii) acetate and N-aryliminopyridines. As demonstrated by TEM, XRD, XPS and Raman spectroscopy, the synthesized material is composed of Fe(0), Fe3C and FeNx in a N-doped carbon matrix. The decent catalytic activity of this robust and easily recyclable Fe-material allowed for the selective hydrogenation of various (iso)quinoline derivatives, even in the presence of reducible functional groups, such as nitriles, halogens, esters and amides. For a proof-of-concept, this nanostructured catalyst was implemented in the multistep synthesis of natural products and pharmaceutical lead compounds as well as modification of photoluminescent materials. As such this methodology constitutes the first heterogeneous iron-catalyzed hydrogenation of substituted (iso)quinolones with synthetic importance.

A General and Highly Selective Cobalt-Catalyzed Hydrogenation of N-Heteroarenes under Mild Reaction Conditions

Herein, a general and efficient method for the homogeneous cobalt-catalyzed hydrogenation of N-heterocycles, under mild reaction conditions, is reported. Key to success is the use of the tetradentate ligand tris(2-(diphenylphosphino)phenyl)phosphine). This non-noble metal catalyst system allows the selective hydrogenation of heteroarenes in the presence of a broad range of other sensitive reducible groups.

Cobalt-catalysed transfer hydrogenation of quinolines and related heterocycles using formic acid under mild conditions

Herein, we report the first example of homogeneous non-noble metal-catalyzed transfer hydrogenation of N-heteroarenes. The combination of Co(BF4)2·6H2O with tris(2-(diphenylphosphino)phenyl)phosphine L1 is able to selectively reduce quinolines in the presence of other sensitive functional groups, under mild conditions, using formic acid as a hydrogen source.

A simple iridicycle catalyst for efficient transfer hydrogenation of n-heterocycles in water

A cyclometalated iridium complex is shown to catalyse the transfer hydrogenation of various nitrogen heterocycles, including but not limited to quinolines, isoquinolines, indoles and pyridinium salts, in an aqueous solution of HCO2H/HCO2Na under mild conditions. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), with catalyst loadings as low as 0.01 mol % being feasible. Mechanistic investigation of the quinoline reduction suggests that the transfer hydrogenation proceeds via both 1,2- and 1,4-addition pathways, with the catalytic turnover being limited by the step of hydride transfer. An easily accessible iridicycle catalyst effects the transfer hydrogenation of a wide variety of N-heterocycles in water, including quinolines, isoquinolines, indoles, quinoxalines, and pyridines. The catalyst shows excellent functional-group compatibility and high turnover number (up to 7500), even with low catalyst loadings.

Selective Catalytic Hydrogenation of Heteroarenes with N-Graphene-Modified Cobalt Nanoparticles (Co3O4-Co/NGratα-Al2O3)

Cobalt oxide/cobalt-based nanoparticles featuring a core-shell structure and nitrogen-doped graphene layers on alumina are obtained by pyrolysis of Co(OAc)2/phenanthroline. The resulting core-shell material (Co3O4-Co/NGratα-Al2O3) was successfully applied in the catalytic hydrogenation of a variety of N-heteroarenes including quinolines, acridines, benzo[h], and 1,5-naphthyridine as well as unprotected indoles. The peculiar structure of the novel heterogeneous catalyst enables activation of molecular hydrogen at comparably low temperature. Both high activity and selectivity were achieved in these hydrogenation processes, to give important building blocks for bioactive compounds as well as the pharmaceutical industry.

The remarkable effect of a simple ion: Iodide-promoted transfer hydrogenation of heteroaromatics

I can do it! Accelerated by simple iodide ions, rhodium-catalysed transfer hydrogenation can be readily performed on quinolines, isoquinolines and quinoxalines, affording the tetrahydro products in high yields with low catalyst loading (see scheme). Copyright