38323-22-7

Basic information

• Product Name: DIMETHYL (4-NITROBENZYLIDENE)MALONATE
• Synonyms: DIMETHYL (4-NITROBENZYLIDENE)MALONATE;(4-Nitrobenzylidene)malonic acid dimethyl ester;[(4-Nitrophenyl)methylene]malonic acid dimethyl ester;2-(4-Nitrobenzylidene)malonic acid dimethyl ester
• CAS NO: 38323-22-7
• Molecular Formula: C₁₂H₁₁NO₆
• Molecular Weight: 265.21884
• Mol File: 38323-22-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 137-139 °C(lit.)
• Boiling Point: 336.4°C at 760 mmHg
• Flash Point: 135°C
• Appearance: /
• Density: 1.335g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: DIMETHYL (4-NITROBENZYLIDENE)MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL (4-NITROBENZYLIDENE)MALONATE(38323-22-7)
• EPA Substance Registry System: DIMETHYL (4-NITROBENZYLIDENE)MALONATE(38323-22-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 38323-22-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H11NO6/c1-18-11(14)10(12(15)19-2)7-8-3-5-9(6-4-8)13(16)17/h3-7H,1-2H3

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 108-59-8 malonic acid dimethyl ester 
• 6773-29-1 dimethyl diazomalonate 
• 6626-84-2 dimethyl 2-benzylidenepropanedioate 
• 7697-37-2 nitric acid 

Downstream Products

• 859200-83-2 (α-methoxy-4-nitro-benzyl)-malonic acid dimethyl ester 
• 111735-90-1 2-[2-Methyl-2-nitro-1-(4-nitro-phenyl)-propyl]-malonic acid dimethyl ester 
• 86661-25-8 2-[(R)-(4-Nitro-phenyl)-((S)-2-oxo-cyclohexyl)-methyl]-malonic acid dimethyl ester 
• 86661-25-8 dimethyl 2-((R)-(4-nitrophenyl)((R)-2-oxocyclohexyl)methyl)malonate 
• 86661-25-8 dimethyl 2‐{(S)‐(4‐nitrophenyl)[(1S)‐2‐oxocyclohexyl]methyl}propanedioate 
• 19310-31-7 methyl (Z)-3-(4-nitrophenyl)-2-propenoate 
• 637-57-0 p-nitrocinnamic acid methyl ester 
• 103883-94-9 2-Bromo-2-[bromo-(4-nitro-phenyl)-methyl]-malonic acid dimethyl ester 
• 197234-78-9 dimethyl 3-[(4-nitro)phenyl]aziridine-2,2-dicarboxylate 
• 510720-43-1 2-[(S)-2-[(E)-(S)-2-(Methoxy-diphenyl-methyl)-pyrrolidin-1-ylimino]-1-(4-nitro-phenyl)-ethyl]-malonic acid dimethyl ester 

Relevant articles and documents

A versatile palladium-mediated three-component reaction for the one-pot synthesis of stereodefined 3-arylidene-(or 3-alkenylidene-)tetrahydrofurans

A one-pot reaction between equimolecular amounts of various propargyl alcohols Michael acceptors, and unsaturated halides (or triflates) in the presence of a palladium(0) catalyst provides a simple and flexible entry into highly substituted 3-arylidene-(or 3-alkenylidene-)tetrahydrofurans. The efficiency of this palladium-mediated three-component reaction has been shown to be strongly influenced by the nature of the catalyst system, and in this regard, a palladium(0) catalyst generated in situ by reduction of PdCl2(PPh3)2 with n-butyllithium has been found particularly effective.

A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates

A novel sublimable organic salt was synthesized, and its chemical structure was characterized by FTIR, 1D NMR, 2D NMR, and elemental analysis. In addition, the thermal phase transitions and thermal stability of new organic salt were investigated. The DSC and TGA results showed that the organic salt could convert into constituent molecules at dec. ~ 200?°C) under atmospheric pressure without forming the liquid phase. Then, it was recondensed to regenerate the initial organic salt in the cool part of the vial. Therefore, it can be a promising organic salt towards the regeneration of spent catalyst from synthesis processes when the reaction mixture contains poorly volatile components and includes its use in gas-phase procedures. Also, the catalytic efficiency of new organic salt was investigated in the Knoevenagel condensation reaction. A variety of substituted arylidene and alkylidene malonates were isolated in 78–95% yield within six hours.? Under the optimized reaction conditions, the current catalytic procedure exhibited superiority compared to the mixed piperazine/acetic acid, piperidine/acetic acid, and piperidinium acetate. There were no significant changes in the new organic salt chemical structure and catalytic activity even after the 5th run. This work revealed the importance of the existence of simultaneous hydrogen bond acceptor/donor groups in our environmentally friendly catalyst to promote the Knoevenagel condensation reaction without the use of metal-containing catalysts.

Synthesis, molecular docking, α-glucosidase inhibition, and antioxidant activity studies of novel benzimidazole derivatives

A novel series of N-methyl/benzyl-substituted benzimidazolyl-linked para-substituted benzyl-based compounds containing 2,4-thiazolidinediones, dimethyl malonate (DMM), and diethyl malonate (DEM) 17–27 were designed, docked, synthesized, and evaluated for their antidiabetic activity studies. Structures of all the synthesized compounds were confirmed through 1H NMR, 13C NMR, FTIR, and mass spectrometry. Four targeted compounds (17–18 and 22–23) showed good inhibitory potential in the range of 4.10 ± 0.01 to 9.12 ± 0.06 μM. Furthermore, synthesized compounds 17–27 were evaluated for their antioxidant potential and compared with standard ascorbic acid and results showed that compound 18 (EC50 = 0.176 ± 0.002 mM) being the most active. Compounds 17–18 and 22–23 exhibited prominent antidiabetic as well as antioxidant activity. Compound 18 was considered a promising candidate for this series. The designed molecules were docked into α-glucosidase protein (PDB Code. 3TOP) to develop a correlation with the α-glucosidase inhibition studies and were also additionally docked into PPARγ proteins (PDB ID: 2PRG) with rosiglitazone (standard drug) to study their PPARγ binding affinity in comparison with rosiglitazone and to classify these compounds for their PPARγ agonistic behavior.