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

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

Uses

Used in Pharmaceutical Industry:
6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE is used as a building block for the synthesis of various drugs and biologically active compounds. Its unique structure allows for the development of new pharmaceuticals with potential therapeutic applications.
Used in Medicinal Chemistry Research:
6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE is used as a research tool in medicinal chemistry to study its potential pharmacological properties, including its effects on the central nervous system, as well as its anti-inflammatory and antioxidant activities.
Used in Chemical Reactions:
6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE is used as a reagent in various chemical reactions, facilitating the synthesis of new compounds and contributing to the advancement of chemical processes.
Used in Drug Discovery:
6-BROMO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE serves as a substrate for the development of new chemical processes and the discovery of novel drug candidates, enhancing the potential for innovative therapeutic interventions.

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

• 912953-25-4 6-[4-(trifluoromethyl)phenyl]-3,4-dihydroquinolin-2(1H)-one 
• 1092523-03-9 6-bromo-1-methyl-3,4-dihydroquinolin-2(1H)-one 
• 70639-77-9 1,2,3,4-tetrahydro-2-oxo-6-quinolinecarboxylic acid 
• 912954-77-9 6-(4-aminophenyl)-3,4-dihydro-2(1H)-quinolinone 
• 124782-95-2 6-bromo-2-(piperazin-1-yl)quinoline 
• 19205-72-2 6-bromo-3,4-dihydroquinolin-2(1H)-thione 
• 1810-71-5 6-bromo-2-chloroquinoline 
• 119924-94-6 3,4-dihydro-6-(1H-imidazol-1-yl)quinolin-2(1H)-one 

Relevant articles and documents

Tetrahydroquinoline-Capped Histone Deacetylase 6 Inhibitor SW-101 Ameliorates Pathological Phenotypes in a Charcot-Marie-Tooth Type 2A Mouse Model

Histone deacetylase 6 (HDAC6) is a promising therapeutic target for the treatment of neurodegenerative disorders. SW-100 (1a), a phenylhydroxamate-based HDAC6 inhibitor (HDAC6i) bearing a tetrahydroquinoline (THQ) capping group, is a highly potent and sel

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.

Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.

Combining Eosin y with Selectfluor: A Regioselective Brominating System for Para-Bromination of Aniline Derivatives

A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.

Substituted indole compounds, as well as using method and application thereof

The invention relates to substituted indole compounds, a using method and application of the substituted indole compounds, as well as a medicine composition including the compounds and application thereof. The compounds or medicine composition can be used for inhibiting reuptake of 5-hydroxytryptamine. The invention further relates to a method for preparing the compounds and the medicine composition, as well as application of the compounds and medicine composition in treatment of central nervous system dysfunction.

Triazole derivative having HSP90 (Heat Shock Protein) inhibiting activity, as well as preparation method and application of triazole derivative

The invention discloses a triazole derivative having an HSP90 (Heat Shock Protein) inhibiting activity, as well as a preparation method and an application of the triazole derivative. Specifically, the invention relates to the triazole derivative having a structure as shown in a formula (I), a stereisomer of the triazole derivative and a pharmaceutically acceptable salt, wherein the definition of each substituent group in the formula (I) and the definition in a description are the same. The compound with a novel structure has the HSP90 inhibiting activity, can be used to cure cancers, neurodegenerative disorders, inflammation diseases, autoimmune diseases, ischemic brain injuries and the like, and has a broad application prospect.

Biocatalytic α-Oxidation of Cyclic Amines and N-Methylanilines for the Synthesis of Lactams and Formamides

An environmentally friendly method for the synthesis of lactams and formamides through the biocatalytic α-oxidation of amines was developed by employing Pseudomonas plecoglossicida ZMU-T04 as a biocatalyst. In this biocatalytic process, the α-oxidation of cyclic amines and N-methylanilines proceeded smoothly to give the corresponding amides in low to high yields. Furthermore, it was demonstrated that synthetic 3,4-dihydroquinolin-2(1H)-one could be used as a key precursor of antidepressant bioactive molecules. The mechanism of this biocatalytic α-oxidation process was investigated by isotope- labeling experiments.

INHIBITORS OF RENAL OUTER MEDULLARY POTASSIUM CHANNEL

Compounds of Formula I and the pharmaceutically acceptable salts thereof are provided as inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.