5495-09-0

Basic information

• Product Name: Quinoxaline, 1,2-dihydro-3-phenyl-
• CAS NO: 5495-09-0
• Molecular Formula: C14H12N2
• Molecular Weight: 208.263
• Mol File: 5495-09-0.mol

Chemical Properties

• CAS DataBase Reference: Quinoxaline, 1,2-dihydro-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoxaline, 1,2-dihydro-3-phenyl-(5495-09-0)
• EPA Substance Registry System: Quinoxaline, 1,2-dihydro-3-phenyl-(5495-09-0)

Safety Data

• Hazardous Substances Data: 5495-09-0(Hazardous Substances Data)

Upstream product

• 5021-43-2 2-phenylquinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 5021-43-2 2-phenylquinoxaline 
• 1222843-82-4 (R)-2-phenyl-1,2,3,4-tetrahydroquinoxaline 
• 1203948-11-1 (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline 
• 5021-47-6 2-phenyl-1,2,3,4-tetrahydro-quinoxaline 
• 1404376-86-8 C₁₄H₁₃⁽²⁾HN₂ 

Relevant articles and documents

Facile Synthesis and Bioactivity of Novel N,N′-disubstituted-1,2,3,4-tetrahydroquinoxalines

A series of novel N,N'-disubstituted-1,2,3,4-tetrahydroquinoxalines were designed and synthesized by cyclization and acylation. The structures of all the novel compounds were confirmed by IR, 1H NMR, 13C NMR, and high-resolution mass

Additive effects of amines on asymmetric hydrogenation of quinoxalines catalyzed by chiral iridium complexes

The additive effects of amines were realized in the asymmetric hydrogenation of 2-phenylquinoxaline, and its derivatives, catalyzed by chiral cationic dinuclear triply halide-bridged iridium complexes [{Ir(H)[diphosphine]} 2(μ-X)3]X (diphosphine=(S)-2,2'-bis(diphenylphosphino)- 1,1'-binaphthyl [(S)-BINAP], (S)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3- benzodioxole [(S)-SEGPHOS], (S)-5,5'-bis(diphenylphosphino)-2,2,2',2'- tetrafluoro-4,4'-bi-1,3-benzodioxole [(S)-DIFLUORPHOS]; X=Cl, Br, I) to produce the corresponding 2-aryl-1,2,3,4-tetrahydroquinoxalines. The additive effects of amines were investigated by solution dynamics studies of iridium complexes in the presence of N-methyl-p-anisidine (MPA), which was determined to be the best amine additive for achievement of a high enantioselectivity of (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline, and by labeling experiments, which revealed a plausible mechanism comprised of two cycles. One catalytic cycle was less active and less enantioselective; it involved the substrate-coordinated mononuclear complex [IrHCl2(2-phenylquinoxaline){(S)-BINAP}], which afforded half-reduced product 3-phenyl-1,2-dihydroquinoxaline. A poorly enantioselective disproportionation of this half-reduced product afforded (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline. The other cycle involved a more active hydride-amide catalyst, derived from amine-coordinated mononuclear complex [IrCl2H(MPA){(S)-BINAP}], which functioned to reduce 2-phenylquinoxaline to (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline with high enantioselectivity. Based on the proposed mechanism, an IrI-JOSIPHOS (JOSIPHOS=(R)-1-[(Sp)-2-(dicyclohexylphosphino)ferrocenylethyl] diphenylphosphine) catalyst in the presence of amine additive resulted in the highest enantioselectivity for the asymmetric hydrogenation of 2-phenylquinoxaline. Interestingly, the reaction rate and enantioselectivity were gradually increased during the reaction by a positive-feedback effect from the product amines. Copyright

A rapid and efficient method for the reduction of quinoxalines

Mono and di-substituted alkyl and aryl quinoxalines are rapidly reduced in high yield to their respective 1,2,3,4-tetrahydro-derivatives by borane in THF solution. In the case of the 2,3-di-substituted compounds, reduction is stereoselective yielding excl

3-ARYL-1,2-DIHYDROQUINOXALINES

The reaction between o-phenylenediamine and its 4-chloro- and 3,5-dichloro-derivatives and 4-substituted ω-bromoacetophenones gives 1,2-dihydroquinoxalines.It has been found that the preferred course of the reaction under basic catalytic conditions involv