18470-23-0

Basic information

• Product Name: QUINOXALINE, 6-BROMO-2,3-DIMETHYL-
• Synonyms: QUINOXALINE, 6-BROMO-2,3-DIMETHYL-
• CAS NO: 18470-23-0
• Molecular Formula: C₁₀H₉BrN₂
• Molecular Weight: 237.11
• Mol File: 18470-23-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: QUINOXALINE, 6-BROMO-2,3-DIMETHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: QUINOXALINE, 6-BROMO-2,3-DIMETHYL-(18470-23-0)
• EPA Substance Registry System: QUINOXALINE, 6-BROMO-2,3-DIMETHYL-(18470-23-0)

Safety Data

• Hazardous Substances Data: 18470-23-0(Hazardous Substances Data)

Upstream product

• 5228-61-5 5-bromo-2-nitroaniline 
• 513-85-9 2.3-butanediol 
• 875-51-4 4-Bromo-2-nitroaniline 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 431-03-8 dimethylglyoxal 
• 2379-55-7 2,3-dimethylquinoxaline 

Downstream Products

• 1225279-41-3 2,3-dimethyl-6-[3-(piperidin-1-ylmethyl)phenyl]quinoxaline 
• 2379-55-7 2,3-dimethylquinoxaline 
• 59417-51-5 1,1-diphenyl-2-(3-methyl-2-quinoxalinyl)ethanol 

Relevant articles and documents

Iron-catalyzed one-pot synthesis of quinoxalines: Transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

Here, we report iron-catalyzed one-pot synthesis of quinoxalines via transfer hydrogenative condensation of 2-nitroanilines with vicinal diols. The tricarbonyl (η4-cyclopentadienone) iron complex, which is well known as the Kn?lker complex, catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding carbonyl and 1,2-diaminobenzene intermediates were generated in situ. Trimethylamine N-oxide was used to activate the iron complex. Various unsymmetrical and symmetrical vicinal diols were applied for transfer hydrogenation, resulting in quinoxaline derivatives in 49-98% yields. A plausible mechanism was proposed based on a series of control experiments. The major advantages of this protocol are that no external redox reagents or additional base is needed and that water is liberated as the sole byproduct. This journal is

Anti-cancer quinoxaline pyrimidinamine heterocyclic compound as well as preparation method and application thereof

The invention discloses an anti-cancer quinoxaline pyrimidinamine heterocyclic compound and a preparation method and application thereof, the structure of the compound is shown as a formula (S), and X is selected from C (O) or (CH2) n; n is 0 or 1; R1 is selected from hydrogen and C1-C8 alkyl; R2 is selected from hydrogen, C1-C8 alkyl, morpholine ring or-NR5R6, and R5 and R6 are selected from hydrogen and C1-C8 alkyl; R3 is selected from hydrogen, methoxyl and halogen; and R4 is selected from hydrogen, C1-C8 alkyl,-S (O) 2Me and-C (O) OC1-C3. The invention also discloses a preparation method and application of the compound.

Quinoxaline compound containing triazine group, quinoxaline composition, electron transport material and electroluminescent device

The invention provides a quinoxaline compound containing a triazine group, a quinoxaline composition, an electron transport material and an electroluminescent device. The quinoxaline compound has a structure as shown in a general formula A. In the general

NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.

Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water

Herein, an efficient methodology for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcohols. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal-ligand cooperative mechanism was proposed based on kinetic and DFT studies.

Polycyclic aromatic hydrocarbon derivative comprising quinoxaline group and application thereof

The invention relates to a polycyclic aromatic hydrocarbon derivative comprising a quinoxaline group. The compound has the structure represented as the formula (I). The polycyclic aromatic hydrocarbon derivative is suitable for being used as an ETL material in electroluminescence displayers. The compound can effectively reduce operating voltage of an organic light-emitting device, and can improve the luminous efficiency of the organic light-emitting device.

An experimental and theoretical study of intramolecular regioselective oxidations of 6-substituted 2,3-dimethylquinoxaline derivatives

An experimental and theoretical study of the regioselective Riley oxidation was conducted on a series of 2,3-dimethyl-6-substituted-quinoxalines bearing EWG (NO2, CN, CF3, Cl, Br, F, COOH, COOMe, COPh) and EDG (2,3-dimethylquinoxaline, OMe, OH, NH2) substituents. The nitrogen lone pair of electrons of the symmetric benzopyrazine moiety initiates the oxidation and promotes nucleophilic competition between the two active sites to give carbaldehyde regioisomers a and b. The mesomeric effect provides the dominant contribution to the regioselectivity. The compounds were characterized by NMR, measuring the 1H, 13C, pfg-HSQC, pfg-HMBC, and 15N, 1H correlation signals established by pfg-HMQC. The nucleophilic reactivity of nitrogen was evaluated by 1H NMR titration and analyzed using Perrin linearization to determine the reactivity ratio, ΔK, of the N4 and N1 nitrogen atoms. The structures were optimized using density functional theory at the ωB97XD/6-311G++(d,p) level of theory. The highest occupied molecular orbitals modeled using the HF/6-311G++(d,p) functionals revealed an asymmetric electron density that confirmed the asymmetric nucleophilicity of the nitrogen centers. These values agreed with the experimentally measured ΔK ratios. The PM6 theoretical calculations of the heats of formation of the mesomeric forms and intermediates of (2,3-dimethyl-6-substituted-quinoxalines)-SeO2 allowed us to identify the reaction routes that minimized energy expenditures. The regioselectivities were explained in terms of the energetic diagrams of the regioisomers. All compounds evaluated indicated a preference toward forming regioisomer b, except for the derivative bearing the EDG substituent (2,3-dimethylquinoxaline) which displayed a preference for regioisomer a.

One-pot synthesis of quinoxalines from reductive coupling of 2-nitroanilines and 1,2-diketones using indium

The one-pot reduction-cyclization of 2-nitroanilines and 1,2-diketones to give quinoxalines was investigated. Using indium and an appropriate acid such as acetic acid or indium(III) chloride, various quinoxaline derivatives including 2,3-dialkylquinoxalines, 2,3-diphenylquinoxalines, 2,3-di-2-thiophenylquinoxalines, 2,3-di(pyridin-2-yl)quinoxalines, and dibenzo[a,c]phenazines were synthesized in moderate to excellent yield.

Microwave-assisted solvent-free synthesis and in vitro antibacterial screening of quinoxalines and pyrido[2, 3b]pyrazines

We report herein the microwave assisted synthesis, without solvents and catalysts, of 6-substituted quinoxalines and 7-substituted pyrido[2,3b] pyrazines. The compounds were obtained in good yields and short reaction times using the mentioned procedure and two new structures are reported. A complete 1H-and 13C-NMR assignment was performed using 1D and 2D-NMR. Additionally, an in vitro screening was performed on Gram-positive and Gram-negative bacteria using amoxicillin as positive reference. Compounds bearing a pyridyl group tended to have higher antibacterial activity, but the best activity against Bacillus subtilis and Proteus mirabilis was observed with quinoxaline derivatives.

Glycerin and CeCl3 7H2O: A new and efficient recyclable reaction medium for the synthesis of quinoxalines

An efficient and environmentally benign process for the synthesis of quinoxalines has been developed using glycerine-cerium chloride as a reaction medium. This method is applicable to a variety of diketones and 1,2-phenylenediamines to afford the corresponding quinoxaline derivatives in excellent yields. The reaction medium was recovered and reused for further reactions without any problem. Taylor & Francis Group, LLC.