3279-90-1

Basic information

• Product Name: 6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE
• Synonyms: 6-BROMO-1,2,3,4-TETRAHYDRO-2-QUINOLINONE;6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE;6-BROMO-3,4-DIHYDRO-2(1H)-QUINOLINONE;6-BROMO-3,4-DIHYDROQUINOLIN-2(1H)-ONE;6-Bromo-3,4-dihydro-2(1H)-quinolinone 98%;2(1H)-Quinolinone, 6-bromo-3,4-dihydro-;6-Bromocarbostiryl;6-BroMo-3,4-dihydro-(1H)-2-quinolinone
• CAS NO: 3279-90-1
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.07
• Mol File: 3279-90-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 170-172℃
• Boiling Point: 376.254 °C at 760 mmHg
• Flash Point: 181.352 °C
• Appearance: Brown/Powder
• Density: 1.559 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 13.92±0.20(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(3279-90-1)
• EPA Substance Registry System: 6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE(3279-90-1)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-52-22
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 3279-90-1(Hazardous Substances Data)

Usage

General Description

6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE is a chemical compound with the molecular formula C9H8BrNO. It is a brominated derivative of quinolinone, a heterocyclic compound. This chemical is commonly used in the pharmaceutical industry as a building block for the synthesis of various drugs and biologically active compounds. It has also been studied for its potential pharmacological properties, including its effects on the central nervous system and its anti-inflammatory and antioxidant activities. Additionally, it has been used as a reagent in chemical reactions and as a substrate for the development of new chemical processes. Its structure and properties make it a valuable tool for the advancement of medicinal chemistry and drug discovery efforts.

InChI:InChI=1/C9H8BrNO/c10-7-2-3-8-6(5-7)1-4-9(12)11-8/h2-3,5H,1,4H2,(H,11,12)

Upstream product

• 42287-90-1 3-(3-bromophenyl)propanoic acid 
• 1643-30-7 3-(4-bromophenyl)propionic acid 
• 335159-82-5 3-(m-bromophenyl)propionyl chloride 
• 55394-81-5 3-(4-bromophenyl)propanoyl chloride 
• 1228680-89-4 3-Bromobenzyl-acetohydroxamic acid 
• 342373-40-4 3-(4-bromophenyl)-N-hydroxypropanamide 
• 22190-35-8 6-bromo-1,2,3,4-tetrahydroquinoline 
• 71861-99-9 formic acid-(2,4-dibromo-anilide) 
• 1536478-47-3 N-(4-bromo-2-vinylphenyl)formamide 
• 3460-04-6 3-chloro-N-phenylpropionamide 
• 62-53-3 aniline 
• 34598-49-7 5-Bromo-1-indanone 
• 857770-64-0 N-(6-bromo-2-oxo-1,2,3,4-tetrahydro-[7]quinolyl)-acetamide 
• 22246-08-8 7-acetylamino-3,4-dihydro-1H-quinolin-2-one 

Downstream Products

• 119924-94-6 3,4-dihydro-6-(1H-imidazol-1-yl)quinolin-2(1H)-one 
• 1810-71-5 6-bromo-2-chloroquinoline 
• 1224927-63-2 tert-butyl 2-(6-bromo-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate 
• 882023-20-3 1-(4-biphenylmethyl)-6-bromo-3,4-dihydro-1H-quinolin-2-one 
• 1616681-00-5 phenyl 2-oxo-1,2,3,4-tetrahydroquinoline-6-carboxylate 
• 1616681-02-7 phenyl 1-butyl-2-oxo-1,2,3,4-tetrahydroquinoline-6-carboxylate 
• 70639-77-9 1,2,3,4-tetrahydro-2-oxo-6-quinolinecarboxylic acid 
• 912953-25-4 6-[4-(trifluoromethyl)phenyl]-3,4-dihydroquinolin-2(1H)-one 
• 124782-95-2 6-bromo-2-(piperazin-1-yl)quinoline 
• 19205-72-2 6-bromo-3,4-dihydroquinolin-2(1H)-thione 
• 912954-77-9 6-(4-aminophenyl)-3,4-dihydro-2(1H)-quinolinone 

Relevant articles and documents

Visible-Light Induced C(sp2)?H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover

We report an approach for the intramolecular C(sp2)?H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C?C bond migration.

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents

A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.