5279-62-9

Basic information

• Product Name: 2-cyano-2-{5-[(4-ethoxy-3-methoxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene}-N-(2-phenylethyl)acetamide
• CAS NO: 5279-62-9
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 525.6181
• Mol File: 5279-62-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 727.4°C at 760 mmHg
• Flash Point: 393.7°C
• Density: 1.29g/cm³
• Vapor Pressure: 5.18E-21mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 2-cyano-2-{5-[(4-ethoxy-3-methoxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene}-N-(2-phenylethyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-2-{5-[(4-ethoxy-3-methoxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene}-N-(2-phenylethyl)acetamide(5279-62-9)
• EPA Substance Registry System: 2-cyano-2-{5-[(4-ethoxy-3-methoxyphenyl)methylidene]-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene}-N-(2-phenylethyl)acetamide(5279-62-9)

Safety Data

• Hazardous Substances Data: 5279-62-9(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 13021-14-2 N-methyl-2,4,6-trimethylaniline 
• 487-68-3 mesytaldehyde 
• 85462-16-4 N-Methyl-O-p-nitrophenylsulphonylhydroxylamine 
• 6784-26-5 2-isocyanato-1,3,5-trimethylbenzene 
• 88-05-1 2,4,6-trimethylaniline 
• 13021-15-3 2,4,6-trimethyl-N,N-dimethylaniline 

Relevant articles and documents

Redox inactive metal ion triggered N-dealkylation by an iron catalyst with dioxygen activation: A lesson from lipoxygenases

Utilization of dioxygen as the terminal oxidant at ambient temperature is always a challenge in redox chemistry, because it is hard to oxidize a stable redox metal ion like iron(iii) to its high oxidation state to initialize the catalytic cycle. Inspired by the dioxygenation and co-oxidase activity of lipoxygenases, herein, we introduce an alternative protocol to activate the sluggish iron(iii) species with non-redox metal ions, which can promote its oxidizing power to facilitate substrate oxidation with dioxygen, thus initializing the catalytic cycle. In oxidations of N,N-dimethylaniline and its analogues, adding Zn(OTf)2 to the [Fe(TPA)Cl2]Cl catalyst can trigger the amine oxidation with dioxygen, whereas [Fe(TPA)Cl2]Cl alone is very sluggish. In stoichiometric oxidations, it has also been confirmed that the presence of Zn(OTf)2 can apparently improve the electron transfer capability of the [Fe(TPA)Cl2]Cl complex. Experiments using different types of substrates as trapping reagents disclosed that the iron(iv) species does not occur in the catalytic cycle, suggesting that oxidation of amines is initialized by electron transfer rather than hydrogen abstraction. Combined experiments from UV-Vis, high resolution mass spectrometry, electrochemistry, EPR and oxidation kinetics support that the improved electron transfer ability of iron(iii) species originates from its interaction with added Lewis acids like Zn2+ through a plausible chloride or OTf- bridge, which has promoted the redox potential of iron(iii) species. The amine oxidation mechanism was also discussed based on the available data, which resembles the co-oxidase activity of lipoxygenases in oxidative dealkylation of xenobiotic metabolisms where an external electron donor is not essential for dioxygen activation.

Cationic Carbon to Nitrogen Rearrangements in the Reactions of N-(Sulfonyloxy)amines with Aldehydes

A series of aromatic and aliphatic aldehydes was reacted with N-((p-nitrobenzenesulfonyl)oxy)methylamine in chloroform.Products resulting from both carbon migration and hydride migration to nitrogen were isolated.The ratios of carbon to hydride migration products were used to clarify the reaction mechanism.The results support a two-step process in which cationic carbon to nitrogen rearrangements is rate determining.