6563-13-9

Basic information

• Product Name: 6-METHOXYQUINOLINE N-OXIDE
• Synonyms: TIMTEC-BB SBB005919;6-METHOXYQUINOLINE N-OXIDE;6-METHOXYQUINOLINE N-OXIDE DIHYDRATE, 98 %;6-METHOXYQUINOLINE N-OXIDE 98%;1-Oxylato-6-methoxyquinoline-1-ium;Nsc77096;Quinoline, 6-methoxy-, 1-oxide;6-methoxy-1-oxidoquinolin-1-ium
• CAS NO: 6563-13-9
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 6563-13-9.mol
• Article Data: 59

Chemical Properties

• Melting Point: 102-104 °C(lit.)
• Boiling Point: 340.1ºC at 760 mmHg
• Flash Point: 159.5ºC
• Appearance: /
• Density: 1.16g/cm3
• Vapor Pressure: 0.000173mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.66±0.30(Predicted)
• CAS DataBase Reference: 6-METHOXYQUINOLINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXYQUINOLINE N-OXIDE(6563-13-9)
• EPA Substance Registry System: 6-METHOXYQUINOLINE N-OXIDE(6563-13-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 6563-13-9(Hazardous Substances Data)

Usage

Description

6-METHOXYQUINOLINE N-OXIDE is a chemical compound with the molecular formula C10H9NO2. It is a derivative of quinoline, featuring a methoxy group at the 6th position and an N-oxide functional group. 6-METHOXYQUINOLINE N-OXIDE has been studied for its standard molar enthalpy of formation using static-bomb calorimetry, indicating its potential applications in various fields.

Uses

Unfortunately, the provided materials do not offer specific applications or industries where 6-METHOXYQUINOLINE N-OXIDE is used. However, based on its chemical structure and properties, it can be inferred that this compound may have potential uses in the following areas:
Used in Pharmaceutical Industry:
6-METHOXYQUINOLINE N-OXIDE could be used as an intermediate or active pharmaceutical ingredient for the development of drugs targeting various diseases, given its unique structure and functional groups.
Used in Chemical Research:
As a quinoline derivative, 6-METHOXYQUINOLINE N-OXIDE may be utilized in chemical research for the synthesis of novel compounds with potential applications in various fields, such as materials science, agrochemicals, or dyes.
Used in Material Science:
6-METHOXYQUINOLINE N-OXIDE might be employed in the development of new materials with specific properties, such as conductivity, magnetism, or optical characteristics, due to its quinoline backbone and N-oxide group.

InChI:InChI=1/C10H9NO2/c1-13-9-4-5-10-8(7-9)3-2-6-11(10)12/h2-7H,1H3

Upstream product

• 5263-87-6 6-methoxy quinoline 
• 13675-92-8 6-nitroquinoline-N-oxide 
• 124-41-4 sodium methylate 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 5467-79-8 2-cyano-6-methoxyquinoline 
• 4789-73-5 2-phenyl-6-methoxyquinoline 
• 13676-00-1 6-methoxy-2(1H)-quinolinone 
• 74857-16-2 quinolin-2-yl 4-methylbenzenesulfonate 
• 74857-07-1 N-(6-methoxy-2-quinolyl)-2-quinolone 
• 74857-06-0 6-methoxy-2-quinolyl-2'-quinolyl ether 
• 5263-87-6 6-methoxy quinoline 
• 476159-12-3 6-methoxy-2-(3-methoxyphenyl)quinoline 
• 64388-15-4 (6-methoxy-2-(4-methoxyphenyl)quinoline) 
• 119990-33-9 2-amino-6-methoxy quinoline 
• 6279-51-2 6-methoxy-4-aminoquinoline 
• 476159-11-2 6-methoxy-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinoline 
• 64388-13-2 2-(4-hydroxy-phenyl)-quinolin-6-ol 
• 199186-66-8 1,2,3,4-tetrahydro-6-methoxy-2-phenylquinoline 

Relevant articles and documents

Energetics of 6-methoxyquinoline and 6-methoxyquinoline N-oxide: The dissociation enthalpy of the (N-O) bond

The standard (p° = 0.1MPa) molar enthalpies of formation, at T = 298.15K, were determined using static-bomb calorimetry for crystalline 6-methoxyquinoline N-oxide (6MeOQUINO), as -(85.6 ± 3.7) kJ·mol-1 and liquid 6-methoxyquinoline (6MeOQUI), -(25.8 ± 2.2)kJ·mol-1. The standard molar enthalpies of sublimation/vaporization, at T = 298.15K, were measured by microcalorimetry and from the enthalpies of formation of the gaseous compounds, the dissociation enthalpy Dm0 of the (N+-O-) dative covalent bond was derived, as (269.2 ± 5.0)kJ·mol-1.

Quinoline Ligands Improve the Classic Direct C?H Functionalisation/Intramolecular Cyclisation of Diaryl Ethers to Dibenzofurans

The C?H functionalisation approach to the synthesis of dibenzofurans is hampered by a number of problems. Herein we describe the evolution of a cheap, bench stable quinoline ligand, which obviates most of the current limitations and allows for a high yielding synthesis of a range of valuable dibenzofurans. Dibenzofurans are important motifs in natural products and compounds with wide biological activity.

Deoxygenative C2-heteroarylation of quinoline N-oxides: Facile access to α-Triazolylquinolines

A metal-and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-Triazoles. A variety of α-Triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.