17972-06-4

Basic information

• Product Name: Ethanamine, N-[(4-methylphenyl)methylene]-
• CAS NO: 17972-06-4
• Molecular Formula: C10H13N
• Molecular Weight: 147.22
• Mol File: 17972-06-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Ethanamine, N-[(4-methylphenyl)methylene]-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanamine, N-[(4-methylphenyl)methylene]-(17972-06-4)
• EPA Substance Registry System: Ethanamine, N-[(4-methylphenyl)methylene]-(17972-06-4)

Safety Data

• Hazardous Substances Data: 17972-06-4(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 75-04-7 ethylamine 

Downstream Products

• 858132-59-9 [PdCl(CH(C₆H₄CH₃)N(C₂H₅)C(C₆H₅)O)]2 
• 1260503-54-5 3-ethyl-1-methyl-2-phenyl-5-pyridin-4-yl-4-p-tolyl-3-imidazolinium-4-carboxylate 
• 1260503-58-9 1-benzyl-3-ethyl-2-phenyl-4-p-tolyl-3-imidazolinium-4-carboxylate 
• 1563186-94-6 C₁₈H₁₉NO₃ 
• 1563186-77-5 C₂₉H₄₅NOSn 

Relevant articles and documents

Mixed carboxylic-sulfonic anhydride in reaction with imines: A straightforward route to water-soluble β-lactams via a Staudinger-type reaction

The first example of employing a mixed carboxylic-sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.

α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction

In the course of synthesizing and testing various "azole-including" cyclic anhydrides in the Castagnoli-Cushman reaction with imines, a remarkably reactive, pyrrole-based anhydride has been identified. It displayed a remarkably efficient reaction with N-alkyl and N-aryl imines, in particular, with "enolizable" α-C-H imines which typically fail to react with a majority of known cyclic anhydrides. The reactivity of this anhydride has been justified by an efficient resonance stabilization of its enol form. This finding expands the existing arsenal of highly reactive cyclic anhydrides and further confirms the importance of anhydride enolization for an efficient Castagnoli-Cushman reaction.