5263-87-6

Basic information

• Product Name: 6-Methoxyquinoline
• Synonyms: 6-METHOXYQUINOLINE;Methoxyquinoline,95%;6-Methoxyquinoline, 98+%;6-quinanisole;6-Methoxyquinoline, 98% 25GR;NSC 1954;6-Methoxy-1-azanaphthalene;6-Methoxyquinoline6-
• CAS NO: 5263-87-6
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 226-077-2
• Product Categories: Quinoline&Isoquinoline;Chemical Amines;Alkoxyquinolines;Quinolines;Amines;Aromatics;Building Blocks;Heterocyclic Building Blocks
• Mol File: 5263-87-6.mol

Chemical Properties

• Melting Point: 18-20 °C(lit.)
• Boiling Point: 140-146 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to cream/Granular Powder
• Density: 1.15 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00272mmHg at 25°C
• Refractive Index: n20/D 1.625(lit.)
• Storage Temp.: 2-8°C
• Solubility: soluble in Alcohol
• PKA: 5.03(at 20℃)
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• BRN: 115244
• CAS DataBase Reference: 6-Methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxyquinoline(5263-87-6)
• EPA Substance Registry System: 6-Methoxyquinoline(5263-87-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26
• WGK Germany: 3
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 5263-87-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
6-Methoxyquinoline is used as a synthetic intermediate for the production of various compounds, including fluorescent sensors, potent inhibitors, and metal-organic complexes.
Used in Fluorescent Sensor Applications:
6-Methoxyquinoline is used as a precursor in the synthesis of fluorescent zinc and chlorine sensors, which are essential tools in detecting and monitoring the presence of these ions in various environments.
Used in Tubulin Polymerization Inhibitors:
6-Methoxyquinoline is used as a precursor for the synthesis of 5-amino-2-aroylquinolines, which are potent tubulin polymerization inhibitors. These inhibitors play a crucial role in disrupting the normal function of tubulin, a protein involved in cell division, and have potential applications in cancer therapy.
Used in Bacterial Infection Treatment:
6-Methoxyquinoline is used as a precursor for the synthesis of 3-fluoro-6-methoxyquinoline derivatives, which act as inhibitors of bacterial DNA gyrase and topoisomerase. These derivatives have the potential to be developed into new antibiotics for treating bacterial infections.
Used in Single-Ion Magnets:
6-Methoxyquinoline is used as a precursor in the synthesis of cobalt-based ternary metal-organic complexes, which exhibit single-ion magnet properties. These complexes have potential applications in the development of advanced magnetic materials and devices.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1584, 1946 DOI: 10.1021/ja01212a062

InChI:InChI=1/C10H9NO/c1-12-9-4-5-10-8(7-9)3-2-6-11-10/h2-7H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 504-63-2 trimethyleneglycol 
• 580-16-5 6-hydroxyquinoline 
• 74-88-4 methyl iodide 
• 14002-34-7 tripropanolamine 
• 100-17-4 para-methoxynitrobenzene 
• 612-57-7 6-chloroquinoline 
• 130-95-0 Quinine 
• 156-87-6 propan-1-ol-3-amine 
• 78827-73-3 C₁₃H₁₄N₂O₃ 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 1611-78-5 1,3-bis-dimethylaminotrimethinium perchlorate 
• 56-81-5 glycerol 
• 51-66-1 4-methoxyacetanilide 

Downstream Products

• 6334-31-2 1-benzoyl-6-methoxy-1,2-dihydro-quinoline-2-carbonitrile 
• 34373-76-7 1-ethyl-6-methoxyquinolin-1-ium iodide 
• 4789-73-5 2-phenyl-6-methoxyquinoline 
• 101441-73-0 3-benzyl-6-methoxy-quinoline 
• 21979-59-9 6-methoxy-(N-methyl-quinolinium iodide) 
• 580-16-5 6-hydroxyquinoline 
• 64165-35-1 5-chloro-6-hydroxyquinoline 
• 119990-33-9 2-amino-6-methoxy quinoline 
• 6279-51-2 6-methoxy-4-aminoquinoline 
• 120-15-0 6-methoxy-1,2,3,4-tetrahydroquinoline 
• 6563-13-9 6-methoxyquinoline N-oxide 
• 204251-23-0 5-chloro-6-methoxy-quinoline 
• 6623-91-2 6-methoxy-5-nitroquinoline 
• 5467-79-8 2-cyano-6-methoxyquinoline 

Relevant articles and documents

A NOVEL ROUTE TO QUINOLINE DERIVATIVES FROM 1,3-PROPANEDIOL AND AMINOARENES: RUTHENIUM CATALYZED HETEROCYCLIZATION UNDER NON-ACIDIC CONDITIONS

Ruthenium trichloride hydrate combined with tributylphosphine catalyzes the reaction between 1,3-propanediol and an aminoarene at 180 deg C, providing a novel route to quinoline derivatives under non-acidic conditions.

Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an Aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines

A highly enantioselective addition of hydroxyquinolines to isatin-derived ketimines has been realized using a quinine-derived thiourea organocatalyst. The reaction affords chiral 3-amino-2-oxindoles bearing a quinoline moiety with a quaternary stereocenter in high yields (up to 98%) and excellent enantioselectivities (up to 99%). Moreover, we can extend this methodology for the enantioselective functionalization of 5-hydroxyisoquinoline. This methodology represents, to the best of our knowledge, the first enantioselective addition of hydroxyquinolines to imines. (Figure presented.).

Picomole-Scale Real-Time Photoreaction Screening: Discovery of the Visible-Light-Promoted Dehydrogenation of Tetrahydroquinolines under Ambient Conditions

The identification of new photocatalytic pathways expands our knowledge of chemical reactivity and enables new environmentally friendly synthetic applications. However, the development of miniaturized screening procedures/platforms to expedite the discovery of photochemical reactions remains challenging. Herein, we describe a picomole-scale, real-time photoreaction screening platform in which a handheld laser source is coupled with nano-electrospray ionization mass spectrometry. By using this method, we discovered an accelerated dehydrogenation pathway for the conversion of tetrahydroquinolines into the corresponding quinolines. This transformation is readily promoted by an off-the-shelf [Ru(bpy)3]Cl2?6 H2O complex in air at ambient temperature in direct sunlight, or with the aid of an energy-saving lamp. Moreover, radical cations and trans-dihydride intermediates captured by the screening platform provided direct evidence for the mechanism of the photoredox reaction.

Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material

The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

CgPhen-DalPhos Enables the Nickel-CatalyzedO-Arylation of Tertiary Alcohols with (Hetero)Aryl Electrophiles

While the Ni-catalyzed cross-coupling of primary or secondary aliphatic alcohols and (hetero)aryl electrophiles is known, related cross-couplings involving tertiary aliphatic alcohols, with a broad scope, are challenging. Herein we disclose that a NiIIprecatalyst featuring the ligand CgPhen-DalPhos is unusual in its ability to promote the C-O cross-coupling of tertiary aliphatic alcohols with (hetero)aryl halides (Cl, Br, and I) or phenol derivatives (OMs and OPiv). An exploration of substrate scope and competition experiments help to shed light on the capabilities and reactivity preferences of this catalyst system.

Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles

Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.

Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles

Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Monomeric vanadium oxide: A very efficient species for promoting aerobic oxidative dehydrogenation of N-heterocycles

Monomeric active species are very interesting in heterogeneous catalysis. In this work, we proposed a method to prepare VOx-NbOy@C catalysts, which involve the one-pot hydrothermal synthesis of inorganic/organic hybrid materials containing V/Nb followed by thermal treatment under a reducing atmosphere. The prepared catalysts were characterized using different techniques, such as high-angle annular dark-field scanning transmission electron microscopy and X-ray absorption fine structure spectroscopy. It was shown that monomeric VOx species were dispersed homogeneously in the catalysts. The VOx-NbOy@C catalysts displayed high performance in the aerobic oxidative dehydrogenation of N-heterocycles to aromatic heterocycles. It was demonstrated that the selectivity of reaction over the catalyst with a very small amount of V (0.07 wt%) was much higher than that over the NbOy@C, and the catalyst also exhibited excellent stability in the reaction. The detailed study indicated that monomeric VO2 species were the most effective for promoting the reaction. This journal is