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
• Article Data: 90

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

Description

6-Methoxyquinoline, also known as an aromatic ether, is a quinoline derivative substituted at position 6 by a methoxy group. It is a colorless to light yellow liquid and serves as a valuable synthetic intermediate in various chemical and pharmaceutical applications.

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

• 6024-94-8 6-methoxy-1,2,3,4-tetrahydro-quinoline; sulfate 
• 100-17-4 para-methoxynitrobenzene 
• 7664-93-9 sulfuric acid 
• 104-94-9 4-methoxy-aniline 
• 56-81-5 glycerol 
• 13460-50-9 metaboric acid 
• 51-66-1 4-methoxyacetanilide 
• 130-95-0 Quinine 
• 580-16-5 6-hydroxyquinoline 
• 74-88-4 methyl iodide 
• 156-87-6 propan-1-ol-3-amine 
• 6563-13-9 6-methoxyquinoline N-oxide 
• 78827-73-3 C₁₃H₁₄N₂O₃ 
• 504-63-2 trimethyleneglycol 

Downstream Products

• 1383253-24-4 6-(4-phenylpiperidin-1-yl)quinoline 
• 241485-06-3 6-(4-phenylpiperazin-1-yl)quinoline 
• 871890-63-0 N-methyl-N-phenyl-6-aminoquinoline 
• 88288-04-4 5-fluoro-6-methoxyquinoline 
• 102181-41-9 N,N-diethyl-4-(6-methoxy-[2]quinolyl)-aniline 
• 861039-28-3 2-(3-chlorophenyl)-6-methoxyquinoline 
• 92855-69-1 2-(6-methoxy-[2]quinolyl)-phenol 
• 6623-91-2 6-methoxy-5-nitroquinoline 
• 120-15-0 6-methoxy-1,2,3,4-tetrahydroquinoline 
• 204251-23-0 5-chloro-6-methoxy-quinoline 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 
• 75414-06-1 6-methoxy-5,6,7,8-tetrahydroquinoline 

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.

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.

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.