54535-21-6

Basic information

• Product Name: diethyl [(benzylamino)methylidene]propanedioate
• CAS NO: 54535-21-6
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.3157
• Mol File: 54535-21-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 367.8°C at 760 mmHg
• Flash Point: 176.2°C
• Density: 1.122g/cm³
• Vapor Pressure: 1.33E-05mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: diethyl [(benzylamino)methylidene]propanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl [(benzylamino)methylidene]propanedioate(54535-21-6)
• EPA Substance Registry System: diethyl [(benzylamino)methylidene]propanedioate(54535-21-6)

Safety Data

• Hazardous Substances Data: 54535-21-6(Hazardous Substances Data)

Upstream product

• 5256-74-6 1,3-diethyl 2-diazopropanedioate 
• 20278-32-4 N-benzylthioformamide 
• 6343-54-0 N-benzylformamide 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 622-30-0 N-benzyl hydroxylalmine 
• 622-79-7 benzyl azide 
• 105-53-3 diethyl malonate 
• 27971-92-2 diethyl 2,2,2-trichloroethylidenepropanedioate 
• 226882-05-9 2-(1-benzylamino-2,2,2-trichloro-ethyl)-malonic acid diethyl ester 
• 94473-55-9 1-benzyl-4,4-bis(ethoxycarbonyl)-4,5-dihydro-1,2,3-triazole 
• 3377-20-6 diethyl methylenemalonate 
• 930-30-3 cyclopent-2-enone 
• 100-46-9 benzylamine 
• 1117-96-0 Diazoethan 

Downstream Products

• 54535-11-4 2-(benzylamino-methylene)-malonic acid monoethyl ester 
• 100-46-9 benzylamine 

Relevant articles and documents

Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones

The development of operationally simple and cost-effective methods for C[sbnd]C bond formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted α-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary, secondary and tertiary thioamides all give enanminones when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, α-diazoketoamides, α-diazoesteramides, α-diazoketosulfones and α-diazomonoketones.

A clay catalyzed method for diethyl 2,2,2- trichloroethylidenepropanedioate, an efficient intermediate for the synthesis of enamino esters

An improved high yielding procedure for diethyl 2,2,2- trichloroethyledinepropanedioate (3) using montmorillonite K-10 catalyst has been described. Various diethyl (substituted aminomethylene)propanedioates (6a-j) have been synthesised in excellent yields starting from propanedioate (3) via addition products (5a-j).

Vibrational Spectroscopy and Conformations of 2-Alkoxycarbonyl-3-aminoacrylic Esters

The i.r., Raman, and 1H n.m.r. spectra of 2-alkoxycarbonyl-3-aminoacrylic esters (IV; R1=H, alkyl, aryl) and those of their N-deuteriated derivatives show that these substances exist in the enamino-ester form with a strong intramolecular hydrogen bond between the cis-NH (or -ND) and CO2R2 groups.Some complexities in the i.r. and Raman bands, and their dependence on solvent polarity, temperature, and aggregation state, indicate the existence of rotational isomerism: conformers (IVa and b) predominate in non-polar media; an additional rotamer (IVd) is also probably present in polar solvents.Conformation (IVb) is preferred in the solid state.Some features of the ν(C=O) bands suggest a weak vibrational coupling between the carbonyls.The validity of the criteria established by Smith and Taylor to ascertain the planarity of these and related substances is discussed, and no significant difference in this respect is considered to exist between compounds (IV) with primary and secondary amino-groups.