1873-55-8

Basic information

• Product Name: 3-METHYLQUINOLINE N-OXIDE
• Synonyms: 3-METHYL-QUINOLINE-1-OXIDE;3-METHYLQUINOLINE N-OXIDE;3-Methyl-1-azanaphthalene N-oxide;3-methyl-1-oxidoquinolin-1-ium
• CAS NO: 1873-55-8
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• Mol File: 1873-55-8.mol
• Article Data: 38

Chemical Properties

• Melting Point: 88-89°C
• Boiling Point: 315 °C at 760 mmHg
• Flash Point: 144.3 °C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0.000831mmHg at 25°C
• Refractive Index: 1.585
• PKA: 1.08±0.30(Predicted)
• BRN: 118125
• CAS DataBase Reference: 3-METHYLQUINOLINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLQUINOLINE N-OXIDE(1873-55-8)
• EPA Substance Registry System: 3-METHYLQUINOLINE N-OXIDE(1873-55-8)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 1873-55-8(Hazardous Substances Data)

Usage

General Description

3-Methylquinoline N-oxide is a chemical compound with the molecular formula C10H9NO. It is a pale yellow solid that is commonly used in chemical synthesis and as a reagent in organic reactions. 3-Methylquinoline N-oxide is a potent inhibitor of human cytochrome P450 1A1 and 1A2 enzymes, which are involved in the metabolism of a wide range of drugs and environmental pollutants. It is also known to exhibit antioxidant and antimicrobial properties, and is being studied for its potential use in pharmaceutical and medical applications. Additionally, this compound has been found to have mutagenic and carcinogenic effects when tested on animals, and thus should be handled with caution in laboratory settings.

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

Upstream product

• 586-96-9 Nitrosobenzene 
• 612-58-8 3-methylquinoline 

Downstream Products

• 2721-59-7 3-methylcarbostyril 
• 137470-10-1 3-methyl-2-tosyloxyquinoline 
• 57876-69-4 2-chloro-3-methyl-quinoline 
• 63136-60-7 4-chloro-3-methylquinoline 
• 1421348-74-4 (+/-)-4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid ethyl ester 
• 1421348-63-1 ethyl (+/-)-4-(1-((3-methylquinolin-2-yl)amino)butyl)benzoate 
• 1421348-75-5 (+/-)-4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoic acid 
• 1421348-76-6 (+/-)-3-{4-[(3,3-dimethyl-cyclobutyl)-(3-methyl-quinolin-2-ylamino)-methyl]-benzoylamino}-propionic acid ethyl ester 
• 1421349-05-4 (+/-)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid trifluoroacetic acid salt 
• 1421348-65-3 methyl 3-(4-(1-((3-methylquinolin-2-yl)amino)butyl)benzamido)propanoate 
• 1421348-64-2 (+/-)-4-(1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid 
• 1421348-25-5 C₂₄H₂₇N₃O₃ 
• 1421348-45-9 C₂₇H₃₁N₃O₃ 
• 1421349-03-2 tert-butyl (+/-)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoate 

Relevant articles and documents

Exogenous-oxidant-and catalyst-free electrochemical deoxygenative C2 sulfonylation of quinoline: N-oxides

An exogenous-oxidant-and catalyst-free electrochemical deoxygenative C2 sulfonylation reaction has been achieved. By employing quinoline N-oxides as the starting materials, the electrochemical C-H sulfonylation of electron-deficient quinolines was indirectly achieved at room temperature and a variety of sulfonylated quinoline derivatives were synthesized in modest to high yield with excellent regioselectivity. Notably, this protocol is the first example for synthesizing sulfonylated electron-deficient heteroarenes/arenes through electrochemistry.

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Metal-free C8-H functionalization of quinolineN-oxides with ynamides

The metal-free C8-H functionalization of quinolineN-oxides with ynamides is unveiled for the first time by the intramolecular Friedel-Crafts-type reaction of quinolyl enolonium intermediates generated from Br?nsted acid-catalyzed addition of quinolineN-ox