14547-98-9

Basic information

• Product Name: Quinoline, 4-methoxy-, 1-oxide
• Synonyms: 4-Methoxy-chinolin-1-oxid;4-‐methoxyquinoline N-‐oxide;4-methoxyquinoline 1-oxide;4-methoxyquinoline N-oxide
• CAS NO: 14547-98-9
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Mol File: 14547-98-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Quinoline, 4-methoxy-, 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 4-methoxy-, 1-oxide(14547-98-9)
• EPA Substance Registry System: Quinoline, 4-methoxy-, 1-oxide(14547-98-9)

Safety Data

• Hazardous Substances Data: 14547-98-9(Hazardous Substances Data)

Usage

General Description

Quinoline, 4-methoxy-, 1-oxide is a chemical compound with the molecular formula C10H9NO2. It is a derivative of quinoline, a heterocyclic aromatic compound. The 4-methoxy substituent and the 1-oxidation give this compound a unique chemical and physical properties. It is often used as a building block in the synthesis of pharmaceuticals and agrochemicals. Additionally, it has been studied for its potential antitumor and antimicrobial activities. Quinoline, 4-methoxy-, 1-oxide is also used in the production of dyes, perfumes, and other organic compounds. Overall, it is a versatile compound with a variety of industrial and research applications.

Upstream product

• 611-36-9 quinolin-4-ol 
• 56-57-5 4-nitroquinoline-N-oxide 
• 611-35-8 4-chloroquinoline 
• 607-31-8 4-methoxyquinoline 
• 186581-53-3 diazomethane 
• 3039-74-5 4-quinolinol 1-oxide 
• 86-98-6 4,7-dichloroquinoline 
• 26707-52-8 7-chloro-4-methoxyquinoline 
• 4637-59-6 4-Chloroquinoline N-oxide 
• 124-41-4 sodium methylate 

Downstream Products

• 607-31-8 4-methoxyquinoline 
• 76278-26-7 4-(4-Methoxy-quinolin-2-yl)-2-phenyl-4H-oxazol-5-one 
• 1444018-39-6 2-(phenylethynyl)-4-methoxyquinoline 
• 4179-37-7 graveolinine 
• 15733-83-2 4-methoxyquinoline-2-carboxylic acid 
• 42712-65-2 4-methoxyquinolin-2-ylamine 
• 74831-34-8 C₂₂H₁₈NO₂ 
• 3475-18-1 4-methoxy-2-phenylquinoline 1-oxide 
• 22680-62-2 4-methoxy-2-phenyl-quinoline 
• 83492-21-1 5-(4-Methoxy-quinolin-2-yl)-2-phenyl-thiazol-4-one 

Relevant articles and documents

Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides

Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.

2-Position-Selective Trifluoromethylthiolation of Six-Membered Heteroaromatic Compounds

The regioselective C-H trifluoromethylthiolation of six-membered heteroaromatic compounds via nucleophilic attack of a CF3S source on the electrophilically activated six-membered heteroaromatic ring was developed. The reaction proceeds in good yield with good functional group tolerance, even on a gram-scale. The key to the successful regioselective transformation is the presence of an additive (2,4-dinitrobenzenesulfonyl chloride). The regioselective trifluoromethylthiolation of quinidine derivative is also demonstrated. Trifluoromethylthiolation, followed by S-oxidation, affords the corresponding sulfones.

Revealing the Macromolecular Targets of Fragment-Like Natural Products

Fragment-like natural products were identified as ligand-efficient chemical matter for hit-to-lead development and chemical-probe discovery. Relying on a computational method using a topological pharmacophore descriptor and a drug database, several macromolecular targets from distinct protein families were expeditiously retrieved for structurally unrelated chemotypes. The selected fragments feature structural dissimilarity to the reference compounds and suitable target affinity, and they offer opportunities for chemical optimization. Experimental confirmation of hitherto unknown macromolecular targets for the selected molecules corroborate the usefulness of the computational approach and suggests broad applicability to chemical biology and molecular medicine. Target acquired: Hitherto unknown macromolecular targets of the fragment-like natural products goitrin, isomacroin, and graveolinine were discovered through the use of a computational target-prediction tool tailored for natural products. The results suggest that such methods will find application in target discovery for natural products and could inspire the design of new chemical entities for chemical biology and molecular medicine.