55687-34-8

Basic information

• Product Name: 6-bromoquinoxalin-2(1H)-one
• Synonyms: 6-bromoquinoxalin-2(1H)-one;6-Bromo-2-hydroxyquinoxaline;6-BROMOQUINOXALIN-2-OL;2(1H)-Quinoxalinone, 6-broMo-;6-broMo-1,2-dihydroquinoxalin-2-one
• CAS NO: 55687-34-8
• Molecular Formula: C₈H₅BrN₂O
• Molecular Weight: 225.04
• Product Categories: organic building block
• Mol File: 55687-34-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 298-300 °C(Solv: acetic acid (64-19-7))
• Appearance: /
• Density: 1.822g/cm³
• Refractive Index: 1.721
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.10±0.70(Predicted)
• CAS DataBase Reference: 6-bromoquinoxalin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromoquinoxalin-2(1H)-one(55687-34-8)
• EPA Substance Registry System: 6-bromoquinoxalin-2(1H)-one(55687-34-8)

Safety Data

• Hazardous Substances Data: 55687-34-8(Hazardous Substances Data)

Usage

General Description

6-bromoquinoxalin-2(1H)-one is a chemical compound with the molecular formula C8H5BrN2O. It is a derivative of quinoxaline, which is a heterocyclic compound containing a benzene and pyrazine rings. The presence of the bromine atom and the carbonyl group make 6-bromoquinoxalin-2(1H)-one a versatile building block for the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and materials. It has also been studied for its potential biological activities, including its antibacterial and antifungal properties. Additionally, its structural motif is of interest in the development of new drugs and bioactive molecules.

InChI:InChI=1/C8H5BrN2O/c9-5-1-2-6-7(3-5)10-4-8(12)11-6/h1-4H,(H,11,12)

Upstream product

• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 98416-75-2 6-Bromo-4-oxy-1H-quinoxalin-2-one 
• 96089-46-2 N-(4-bromo-2-nitrophenyl)-3-oxobutanamide 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 1486183-97-4 ethyl 2-(5-brom9-2-nitro-anilino)acetate 
• 854584-01-3 6-bromo-3,4-dihydroquinoxalin-2(1H)-one 
• 924-44-7 glyoxylic acid ethyl ester 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 

Downstream Products

• 305790-88-9 isopropyl 7-bromo-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate 
• 305790-72-1 Isopropyl 7-(3-chlorophenyl)-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate 
• 1228633-28-0 C₂₈H₂₈N₈ 
• 1261071-90-2 C₄₄H₅₈N₈O₅Si 
• 1261071-89-9 C₃₂H₃₈BN₅O₄ 
• 1261071-88-8 C₂₆H₂₆BrN₅O₂ 
• 1228552-66-6 methyl ((S)-1-((S)-2-(4-(4-(6-(2-((S)-1-((methoxycarbonyl)-L-valyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)quinoxalin-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate 
• 1416806-32-0 C₁₉H₁₂F₄N₂O 
• 1416806-14-8 C₁₇H₉BrF₄N₂O 
• 1416806-13-7 C₁₆H₇BrF₄N₂O 
• 175858-10-3 2,6-dibromoquinoxaline 
• 1261072-54-1 methyl {(2S)-1-[(2S)-2-{5-[4-(6-bromoquinoxalin-2-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate 
• 1261071-94-6 2-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}-6-(4-{2-[(2S)-pyrrolidin-2-yl]-1H-imidazol-5-yl}phenyl)quinoxaline 
• 1261070-29-4 methyl {(2S)-1-[(2S)-2-{5-[4-(2-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methyl-butanoyl}pyrrolidin-2-yl]-1H-imidazol-5-yl}quinoxalin-6-yl)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate 

Relevant articles and documents

Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones

Herein, we report a practical electro-reductive protocol for the direct C–H cyanoalkylation of quinoxalin-2(1H)-ones via iminyl radical-mediated ring opening. These mild reactions proceed under metal-, reductant-, and reagent-free conditions to provide synthetically useful cyanoalkylated quinoxalin-2(1H)-ones.

K2S2O8-catalyzed highly regioselective amidoalkylation of diverse N-heteroaromatics in water under visible light irradiation

A K2S2O8-catalyzed versatile C(sp2)-C(sp3) bond formation with N-heteroaromatics and γ-lactams/amides was developed. Quinoxalin-2(1H)-one, quinoline, isoquinoline, phthalazine, and benzothiazole reacted with γ-lactams/amides to give the corresponding C(sp2)-H amidoalkylation products in moderate to good yields with high regioselectivity. This visible-light-induced photocatalyst-free reaction was conducted in H2O at ambient temperature, which comply with the principles of "green chemistry". The new K2S2O8 catalytic mechanism was investigated with control experiments.

N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes

Aiming at the valuable methylation process, readily available and inexpensive N,N,N′,N′-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.