62166-65-8

Basic information

• Product Name: 2-(p-tolyl)iminomalononitrile
• CAS NO: 62166-65-8
• Molecular Weight: 169.186
• Mol File: 62166-65-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(p-tolyl)iminomalononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(p-tolyl)iminomalononitrile(62166-65-8)
• EPA Substance Registry System: 2-(p-tolyl)iminomalononitrile(62166-65-8)

Safety Data

• Hazardous Substances Data: 62166-65-8(Hazardous Substances Data)

Upstream product

• 16728-84-0 p-tolylaminoacetonitrile 
• 24764-92-9 1,4-bis(p-tolyl)-1,4-diaza-1,3-butadiene 
• 670-54-2 ethenetetracarbonitrile 
• 785-86-4 1,3-di(p-tolyl)triaz-1-ene 
• 10153-22-7 N-(4-methoxy-phenyl)-N'-p-tolyl-triazene 

Relevant articles and documents

Synthesis of aryliminoacetonitriles under FVT conditions or by dehydrogenation of arylaminoacetonitriles: an NMR and UV-photoelectron spectroscopy study

The synthesis of [(E)-arylimino]-acetonitriles 3 has been described. It was found that the title compounds can be obtained on the three ways, namely by: (i) dehydrogenation of arylaminoacetonitriles 1, (ii) thermal fragmentation of 1-aryl-4-cyano-β-lactams 4 and (iii) retro-ene reaction of (allyl-p-methoxyphenyl-amino)-acetonitrile (7a) under FVT conditions. 1H and 13C NMR spectra of compounds 3, 5 and 6, and all their precursors 1 and 4, were recorded and analysed in detail using chemical shifts δH and δC [from GIAO DFT B3LYP/6-31(d) calculations] and J-couplings predicted at the DFT B3LYP/IGLO-II level. Also, UV-photoelectron spectra of 4a,d and 3a,d were measured and analysed considering the theoretical evaluation of their ionisation potentials.

Mechanism of the Reaction of 1,3-Diaryltriazenes with Tetracyanoethylene in the Presence of Acetic Acid

The mechanism for the reaction of 1,3-diaryltriazenes with tetracyanoethylene (TCNE) in the presence of acetic acid, giving Schiff's bases and arylhydrazonomalonitriles, has been investigated.The intermediacy of arylazomalononitriles was confirmed by crossover experiments using an arylamine different from the component of the triazene.The route to the azo compounds via TCNE-triazene adducts had already been established by a tracer experiment using an 15N-labelled triazene.However, the crossover experiments, as well as the result of the reaction of a triazene with the TCNE-2,6-dimethylaniline adduct, revealed an alternative route via TCNE-ArNH2 adducts in the presence of acetic acid.