27667-34-1

Basic information

• Product Name: 4-Methoxy-1H-quinolin-2-one
• Synonyms: 4-Methoxy-1H-quinolin-2-one;2(1H)-Quinolinone, 4-methoxy-;4-Methoxy-quinolin-2-ol
• CAS NO: 27667-34-1
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18396
• Product Categories: Quinoline series
• Mol File: 27667-34-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 271 °C
• Boiling Point: 398 °C at 760 mmHg
• Flash Point: 194.5 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 1.52E-06mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: 2-8°C
• PKA: 10.86±0.70(Predicted)
• CAS DataBase Reference: 4-Methoxy-1H-quinolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-1H-quinolin-2-one(27667-34-1)
• EPA Substance Registry System: 4-Methoxy-1H-quinolin-2-one(27667-34-1)

Safety Data

• Hazardous Substances Data: 27667-34-1(Hazardous Substances Data)

Usage

General Description

4-Methoxy-1H-quinolin-2-one, also known as 4-Methoxy-1H-quinolin-2(1H)-one or 4-Methoxyquinolin-2(1H)-one, is an organic compound that belongs to the class of quinolone molecules. It has the chemical formula C10H9NO2 and a molecular weight of 175.18 g/mol. This chemical is a quinolone alkaloid with a methoxy group attached to the quinoline ring, and it is commonly found in various natural sources such as plants and microorganisms. It has shown potential for various biological activities, including antiviral, antibacterial, and antifungal properties. Additionally, 4-Methoxy-1H-quinolin-2-one has been studied for its potential use in pharmaceutical and medicinal applications.

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

Upstream product

• 703-61-7 2,4-dichloroquinoline 
• 5369-62-0 (+/-)-3,3-dimethyloxirane-2-carboxaldehyde 
• 98751-18-9 3-Iodo-4-methoxy-2(1H)-quinolinone 

Downstream Products

• 32262-18-3 N-methyl-4-methoxyquinolin-2(1H)-one 
• 40335-00-0 2,4-dimethoxyquinoline 
• 32606-03-4 1,3,3-Trimethyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline 
• 32606-04-5 1,3-Dimethyl-4-methoxy-2-quinolone 
• 484-29-7 dictamnine 
• 934687-51-1 4-methoxy-6-nitro-1H-quinolin-2-one 

Relevant articles and documents

Synthesis and characterization of substituted 4-methoxy-1H-quinolin-2- thiones

The synthesis of various substituted 4-methoxy-1H-quinolin-2-thiones from various substituted aniline with malonic acid, phosphorousoxychloride, sodium methoxide glacial acetic acid and thiourea under different conditions is described. All these substituted 4-methoxy-1H-quinolin-2-thiones were synthesized from four steps; the first step involved the synthesis of substituted 2,4-dichloro quinoline from aniline (substituted), with malonic acid and phosphorous-oxychloride. In the second step, the substituted 2,4-dichloro compound was heated with freshly prepared methanolic sodium methoxide solution to give 2,4-dimethoxy quinoline compounds, it was then refluxed with glacial acetic acid and hydrochloric acid to get the substituted 4-methoxy-1H-quinolin- 2-one. The final steps involves with an objective of introducing a chloro in the position 2 of the quinolone system, the substituted 4-methoxy-1H-quinolin-2-one was refluxed with distilled PoCl3 chloroform. The substituted 2-chloro-4-methoxy quinoline was then refluxed with thiourea and alcohol to get substituted 4-methoxy-1H-quinolin-2-thiones. The purity of the synthesized compound was judged by their C, H and N analysis and the structure was analyzed on the basics of mass, FT-IR and 1H NMR.

Synthesis of (+)-myrtopsine, (+)-7,8-dimethoxymyrtopsine, and related 2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methyl-ethyl)benzofuran natural products

The first syntheses of myrtopsine (8t) and 7,8-dimethoxymyrtopsine (9t) have been carried out by halogen-metal exchange of 3-iodo-4-methoxy-quinolin-2(1H)-ones (15) and (21) with i-PrMgCl followed by addition of 3,3-dimethyloxirane-2-carboxaldehyde (1). A two-step sequence leads selectively to trans-2,3-dihydro-3-hydroxy-2-(1-hydroxy-1-methylethyl)benzofurans (7t), (8t), (9t), (28), and (32) by conversion of a 2-iodophenol or a 3-iodo-4-methoxyquinolin-2(1H)-one to an aryl Grignard reagent and addition of 3-methyl-2-butenal, followed by threo selective epoxidation of the resulting allylic alcohol and cyclization with inversion.