78596-42-6

Basic information

• Product Name: diethyl {[(4-nitrophenyl)amino]methylidene}propanedioate
• Synonyms: Diethyl {[(4-nitrophenyl)amino]methylene}malonate; propanedioic acid, 2-[[(4-nitrophenyl)amino]methylene]-, diethyl ester
• CAS NO: 78596-42-6
• Molecular Formula: C₁₄H₁₆N₂O₆
• Molecular Weight: 308.2866
• Mol File: 78596-42-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 404.9°C at 760 mmHg
• Flash Point: 198.7°C
• Density: 1.302g/cm³
• Vapor Pressure: 9.11E-07mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: diethyl {[(4-nitrophenyl)amino]methylidene}propanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl {[(4-nitrophenyl)amino]methylidene}propanedioate(78596-42-6)
• EPA Substance Registry System: diethyl {[(4-nitrophenyl)amino]methylidene}propanedioate(78596-42-6)

Safety Data

• Hazardous Substances Data: 78596-42-6(Hazardous Substances Data)

Upstream product

• 100-01-6 4-nitro-aniline 
• 105-53-3 diethyl malonate 
• 149-73-5 trimethyl orthoformate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 103514-53-0 6-nitro-4-hydroxy-quinoline-3-carboxylic acid ethylester 
• 100-01-6 4-nitro-aniline 
• 13675-94-0 4-chloro-6-nitroquinoline 
• 21873-49-4 6-nitroquinoline-4(1H)-one 
• 1415327-30-8 2-[(4-nitro-phenylamino)-methylene]-malonic acid monoethyl ester 
• 103514-54-1 Ethyl 4-chloro-6-nitro-quinoline-3-carboxylate 
• 103514-53-0 ethyl 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 35973-24-1 6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 105168-86-3 C₁₉H₂₄N₄O₈ 
• 103975-92-4 2-[(4-aminophenylamino)methylene]malonic acid diethyl ester 

Relevant articles and documents

Rapid room temperature liquid phase synthesis of diethyl 2-((4-nitroanilino) methylene)malonate

Diethyl 2-((4-nitroanilino)methylene)malonate [4-NANM-E] is an important molecule owing to its role of precursor in the multistage synthesis of several quinoline derivatives possessing biological activities such as antiviral, immunosuppressive, anticancer and photoprotector. This molecule is usually synthesized by a nucleophilic vinyl substitution (SNV) between 4-nitroaniline and diethylethoxymethylene malonate (EMA). Although several procedures are available to synthesize 4-NANM-E in liquid phase, more convenient method is necessary to synthesize in less reaction time and at room temperature. In this study, it is demonstrated that equimolar amounts of EMA and 4-nitroaniline dissolved in alcoholic KOH react within a few seconds at room temperature to produce 4-NANM-E which is purified by simple filtration after acidification with aqueous HCl and washing with alcohol. The reaction has the yield varying at the range 45-53% when it occurs in ethanol, 2-propanol, 2-butanol or 2-pentanol. Therefore, this synthesis method is an excellent alternative to produce 4-NANM-E on an industrial scale.

Easy-to-access quinolone derivatives exhibiting antibacterial and anti-parasitic activities

The cell wall of Mycobacterium tuberculosis (Mtb) has a unique structural organisation, comprising a high lipid content mixed with polysaccharides. This makes cell wall a formidable barrier impermeable to hydrophilic agents. In addition, during host infection, Mtb resides in macrophages within avascular necrotic granulomas and cavities, which shield the bacterium from the action of most antibiotics. To overcome these protective barriers, a new class of anti-TB agents exhibiting lipophilic character have been recommended by various reports in literature. Herein, a series of lipophilic heterocyclic quinolone compounds was synthesised and evaluated in vitro against pMSp12::GFP strain of Mtb, two protozoan parasites (Plasmodium falciparum and Trypanosoma brucei brucei) and against ESKAPE pathogens. The resultant compounds exhibited varied anti-Mtb activity with MIC90 values in the range of 0.24-31 μM. Cross-screening against P. falciparum and T.b. brucei, identified several compounds with antiprotozoal activities in the range of 0.4-20 μM. Compounds were generally inactive against ESKAPE pathogens, with only compounds 8c, 8g and 13 exhibiting moderate to poor activity against S. aureus and A. baumannii.

Insights into supramolecular assembly formation of diethyl aryl amino methylene malonate (DAM)derivatives assisted via non-covalent interactions

The crystal structures of four derivatives of diethyl 2-(((aryl)amino)methylene)malonate (DAM)have been studied by single crystal X-ray diffraction. The molecular structures of all the four derivatives were found to be in co-planar conformation. The detailed analysis of molecular conformation in four derivatives reveals the presence of a common strong intramolecular N–H?O hydrogen bonding, forming a ring of graph-set motif S1 1 (6). The effect of chloro and nitro substitution on their relative strengths of hydrogen bonding are analyzed here. Particularly, in compound 1, additional intramolecular hydrogen bonding between –NO2 and N–H was observed that results in the formation of another six-membered chelate ring. On the other hand in case of compound 3, we have observed type-I Cl?Cl interaction for the first time in this class of compounds. Further, Hirshfeld surface has been generated that is mapped with dnorm shape index and curvedness to summarize the weak interactions and examine the molecular shapes in all four derivatives. Effect of nitro (1 and 2)and chloro (3 and 4)substitution on the C?H, N?O and C?O interaction is highlighted in molecular contour and 2D fingerprint plots.