22615-00-5

Basic information

• Product Name: 3-Bromoquinoline-1-oxide
• Synonyms: 3-bromo-1-oxidoquinolin-1-ium;Quinoline, 3-bromo-,1-oxide
• CAS NO: 22615-00-5
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• Mol File: 22615-00-5.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 358.3°C at 760 mmHg
• Flash Point: 170.5°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 5.32E-05mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: 3-Bromoquinoline-1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromoquinoline-1-oxide(22615-00-5)
• EPA Substance Registry System: 3-Bromoquinoline-1-oxide(22615-00-5)

Safety Data

• Hazardous Substances Data: 22615-00-5(Hazardous Substances Data)

Usage

General Description

3-Bromoquinoline-1-oxide is a chemical compound with the molecular formula C9H6BrNO. It is a yellow crystalline solid that is commonly used as a synthetic intermediate in the production of various pharmaceuticals and agrochemicals. 3-Bromoquinoline-1-oxide is a heterocyclic compound derived from quinoline, and it is known for its strong oxidizing properties. It is also used as a reagent in organic synthesis and in the development of new chemical compounds. Additionally, 3-Bromoquinoline-1-oxide has been studied for its potential applications in the field of medicinal chemistry, including anti-inflammatory, antibacterial, and anticancer properties. Overall, this compound plays a crucial role in the development and production of a wide range of important chemical and pharmaceutical products.

InChI:InChI=1/C9H6BrNO/c10-8-5-7-3-1-2-4-9(7)11(12)6-8/h1-6H

Upstream product

• 5332-24-1 3-bromoquinoline 
• 58550-94-0 3-bromo-1-oxy-quinolin-4-ylamine 
• 2508-86-3 4-aminoquinoline 1-oxide 

Downstream Products

• 3749-18-6 3-bromo-6-nitroquinoline-N-oxide 
• 101422-51-9 1-benzoyloxy-3-bromo-6-nitro-1H-quinolin-2-one 
• 59119-39-0 2-(3-morpholin-4-yl-quinolin-2-yl)-cyclohexanone 
• 52448-21-2 3-phenyl-3H-oxazolo[4,5-b]quinolin-2-one 
• 76278-28-9 4-(3-Bromo-quinolin-2-yl)-2-phenyl-4H-oxazol-5-one 
• 83492-23-3 5-(3-Bromo-quinolin-2-yl)-2-phenyl-thiazol-4-one 
• 74421-87-7 3-(phenylcyanomethyl)-quinoline 1-oxide 
• 83819-56-1 4-(3-bromo-2-quinolyl)dimedone 
• 83819-55-0 3-acetoxy-2-(3-bromo-2-quinolyl)-5,5-dimethyl-2-cyclohexanone 
• 81327-24-4 2-(3-Bromo-1-oxy-quinolin-2-yl)-1-phenyl-ethanone 
• 939-16-2 3-bromoquinolin-2-one 
• 137470-12-3 N-(3-bromo-2-quinolyl)-3-bromo-2-quinolinone 
• 59953-98-9 3-hydroxyquinoline-1-oxide 
• 1132638-64-2 (1-benzylpiperidin-4-yl)-(4-nitro-1-oxyquinolin-3-yl)-amine 

Relevant articles and documents

A concise synthesis of a novel antiangiogenic tyrosine kinase inhibitor

(Chemical Equation Presented). An efficient synthesis of the potent KDR inhibitor 3-[5-[[4-(methylsulfonyl)-1-piperazinyl]methyl]-1H-indole-2-yl] quinolin-2(1H)-one (1) is described. The process features a noncryogenic indole boronation and a dicyclohexylamine-mediated Suzuki coupling.

Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic N-Oxides

An efficient and green electrochemical N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method, sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of the difluoromethyl moiety, and various N-ortho-selective difluoromethylation quinoline and isoquinoline N-oxides were obtained in good to excellent yields under a constant current. In addition, the reaction was easy to scale up and maintained a good yield. Preliminary mechanism studies suggested that the reaction undergoes a free-radical addition and hydrogen elimination pathway.

Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions

An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44–99 %) and with significant enantiomeric excess (70–99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.

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.