6323-89-3

Basic information

• Product Name: 3-(2-phenylethenyl)quinoxalin-2(1H)-one
• CAS NO: 6323-89-3
• Molecular Formula: C₁₆H₁₂N₂O
• Molecular Weight: 248.2793
• Mol File: 6323-89-3.mol
• Article Data: 9

Chemical Properties

• Density: 1.17g/cm³
• Refractive Index: 1.634
• CAS DataBase Reference: 3-(2-phenylethenyl)quinoxalin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-phenylethenyl)quinoxalin-2(1H)-one(6323-89-3)
• EPA Substance Registry System: 3-(2-phenylethenyl)quinoxalin-2(1H)-one(6323-89-3)

Safety Data

• Hazardous Substances Data: 6323-89-3(Hazardous Substances Data)

Upstream product

• 32601-86-8 2-chloro-3-methylquinoxaline 
• 100-52-7 benzaldehyde 
• 14003-34-0 3-methylquinoxalin-2-ol 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 113-24-6 sodium pyruvate 
• 95-54-5 1,2-diamino-benzene 
• 1029476-71-8 3-(α-chlorophenylethyl)quinoxalin-2(1H)-one 

Downstream Products

• 53046-99-4 1-Phenyl-2(3-chlorchinoxal-2-yl)ethen 
• 49568-76-5 3-benzoylquinoxalin-2(1H)-one 
• 1253932-74-9 6-chloro-N-[3-(2-(phenyl)ethenyl)quinoxalin-2(1H)-ylidene]-1,3-benzothiazol-2-amine 
• 366018-66-8 2-phenylsulphonyl-3-styrylquinoxaline 
• 366018-62-4 2-phenylthio-3-styrylquinoxaline 

Relevant articles and documents

Quinoxaline-PABA bipartite hybrid derivatization approach: Design and search for antimicrobial agents

In an attempt to find a new class of antimicrobial agents, in the present study we report the synthesis of bipartite hybrid styryl derivatives of quinoxaline containing para-aminobenzoic acid (PABA) and their biological evaluation as antimicrobial agents. The series of new substituted styryl based derivatives 5(a–k) were evaluated for antimicrobial potential against various bacteria including Staphylococcus aureus, Vibrio cholerae, Escherichia coli, Bacillus subtilis, Escherichia coli, Mycobacterium smegmatis, Pseudomonas aeruginosa and fungi; C. albicans, with ampicillin and amphotericin B as standards. Similarly these compounds were also screened for anti-cancer activity using MCF-7 cell line. Among the synthesized compounds, 5(c) was observed to be the most active compound against various strains with MIC in a range of 7.9–31 μM of the series and compound 5i came out with significant anti-cancer activity with IC50 value of 7 μM.

Multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones in an aqueous medium

A multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones is described. Sequential reactions of o-phenylenediamine with sodium pyruvate and aldehydes in 20% aqueous acetic acid containing sodium acetate provided the target products in good to high yields. The reaction is proposed to proceed via initial condensation of the diamine and pyruvate partners followed by an aldol condensation-type mechanism.

A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments

A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.