21453-02-1

Basic information

• Product Name: 2(1H)-Quinoxalinone, 3-(4-bromophenyl)-
• CAS NO: 21453-02-1
• Molecular Formula: C14H9BrN2O
• Molecular Weight: 301.142
• Mol File: 21453-02-1.mol

Chemical Properties

• CAS DataBase Reference: 2(1H)-Quinoxalinone, 3-(4-bromophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Quinoxalinone, 3-(4-bromophenyl)-(21453-02-1)
• EPA Substance Registry System: 2(1H)-Quinoxalinone, 3-(4-bromophenyl)-(21453-02-1)

Safety Data

• Hazardous Substances Data: 21453-02-1(Hazardous Substances Data)

Upstream product

• 20201-26-7 ethyl 4-bromophenylglyoxylate 
• 95-54-5 1,2-diamino-benzene 
• 7099-87-8 4-bromophenylglyoxylic acid 
• 99-73-0 para-bromophenacyl bromide 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 5467-74-3 4-Bromophenylboronic acid 
• 106-40-1 4-bromo-aniline 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 73387-60-7 1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one 
• 264881-99-4 methyl 2-(4-bromophenyl)-2-diazoacetate 
• 57699-28-2 methyl 4-bromophenylglyoxalate 
• 766-96-1 4-bromo-1-ethynylbenzene 

Downstream Products

• 1255772-46-3 3-(4-bromophenyl)-1-methylquinoxalin-2(1H)-one 
• 354771-48-5 2-(4-bromophenyl)-3-phenylquinoxaline 

Relevant articles and documents

Microwave-Assisted Synthesis of Heterocycles from Aryldiazoacetates**

Herein, we describe a rapid microwave-assisted, metal-free synthesis of substituted quinoxalinones and quinoxalines using the carbene-mediated reaction between aryldiazo esters and 1,2-diamines. The reaction can encompass a range of substituents and structural variations to afford quinoxalin-2-ones in 14–80 % yield and corresponding quinoxalines in good to excellent yields upon oxidation (67–96 %). The approach can be employed to generate symmetrical and unsymmetrical 2,3-diarylquinoxalines, bis-quinoxalines as well as novel quinoxaline-substituted diazo esters and should be a valuable addition to the heterocycle synthesis toolbox.

Metal-free sp3 C-H bond oxidation and functionalization of α-bromoketones to quinoxalinone, benzoxazinone, and benzothiazinone heterocyclic compounds

A series of heterocyclic compounds (benzothiazinones, benzoxazinones and quinoxalinones) were efficiently synthesized in excellent yields via α-bromoketones with o-substituted aniline (2-aminothiophenol, aryl-1,2-diamines and 2-aminophenol). This protocol accomplishes sp3 C-H bond oxidation and functionalization in one-pot without any metal catalyst.

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

K2S2O8 mediated C-3 arylation of quinoxalin-2(1H)-ones under metal-, photocatalyst- And light-free conditions

Two facile and effective C-3 arylation protocols of quinoxalin-2(1H)-ones with arylhydrazines and aryl boronic acids respectively via free radical cross-coupling reactions under metal-, photocatalyst- and light-free conditions have been unveiled. K2

Compound containing fused ring structure and application thereof, and organic electroluminescent device (by machine translation)

The invention relates to the field, of organic electroluminescent devices, and discloses a compound containing a fused ring structure and application thereof, and an organic electroluminescent device, which has a suitable (I) energy level, level HOMO and

A niobium-catalyzed coupling reaction of α-keto acids with: Ortho -phenylenediamines: Synthesis of 3-arylquinoxalin-2(1 H)-ones

A general methodology to access valuable 3-arylquinoxalin-2(1H)-ones was developed, by the reaction of α-keto acids with ortho-phenylenediamines in the presence of ammonium niobium oxalate (ANO) as a catalyst. The reactions were conducted in only 10 min under ultrasonic irradiation as an alternative energy source, affording water as the only co-product. A total of twenty-three different 3-arylquinoxalin-2(1H)-ones were selectively obtained in good to excellent yields by this atom-efficient protocol. Additionally, 1H-15N HMBC experiments were used to reveal the regioisomerism of the obtained products.

Electrochemical Cross-Coupling of C(sp2)?H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach

Photoredox-based C?H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp2)?H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp2)?H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. (Figure presented.).

Ambient and aerobic carbon-carbon bond cleavage toward α-ketoester synthesis by transition-metal-free photocatalysis

The α-oxoesterification of the CC double bond in readily available enaminones enabling efficient synthesis of α-ketoesters is developed. The reactions showing general tolerance to the reactions of primary and secondary alcohols proceed well under air via Rose Bengal (RB)-based photocatalysis. Particularly, this mild synthetic method has been discovered to tolerate various polyhydroxylated substrates such as phenolic alcohol, diols and triols with an excellent selectivity of mono-oxoesterification. What is more noteworthy is that α-ketoester functionalized 16-dehydropregnenolone acetate resulting from the elaboration on a natural product has been obtained practically.

Transition Metal-Free Direct C-3 Arylation of Quinoxalin-2(1H)-ones with Arylamines under Mild Conditions

A transition metal-free direct C-3 arylation of quinoxalin-2(1H)-ones with arylamines has been explored. This reaction proceeded smoothly through a radical process under mild conditions and produced the desired arylation products in good yields. The reactions proceeded efficiently with a broad range of substrates and functional group tolerance. (Figure presented.).