74313-93-2

Basic information

• Product Name: dimethyl (3-nitrobenzylidene)propanedioate
• CAS NO: 74313-93-2
• Molecular Formula: C₁₂H₁₁NO₆
• Molecular Weight: 265.2188
• Mol File: 74313-93-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 354.2°C at 760 mmHg
• Flash Point: 146.8°C
• Density: 1.335g/cm³
• Vapor Pressure: 3.41E-05mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: dimethyl (3-nitrobenzylidene)propanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (3-nitrobenzylidene)propanedioate(74313-93-2)
• EPA Substance Registry System: dimethyl (3-nitrobenzylidene)propanedioate(74313-93-2)

Safety Data

• Hazardous Substances Data: 74313-93-2(Hazardous Substances Data)

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 859194-81-3 (3,α'-dinitro-bibenzyl-α-yl)-malonic acid dimethyl ester 
• 107610-38-8 2-hydroxy-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-5-<2-(2-thienyl)ethoxycarbonyl>-1,4-dihydropyridine 
• 126397-26-0 2-[1-Amino-eth-(E)-ylidene]-4-methoxycarbonyl-3-(3-nitro-phenyl)-pentanedioic acid dimethyl ester 
• 22985-38-2 [2-bromo-2-nitro-1-(3-nitro-phenyl)-ethyl]-malonic acid dimethyl ester 
• 22985-42-8 bromo-[2-nitro-1-(3-nitro-phenyl)-ethyl]-malonic acid dimethyl ester 
• 215316-71-5 (+/-)-3-(3-nitrophenyl)pentanoic acid 
• 107610-39-9 5-cyclopropylmethyloxycarbonyl-2-hydroxy-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine 
• 107610-56-0 2-Chloro-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-cyclopropylmethyl ester 3-methyl ester 
• 107610-55-9 2-Chloro-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-methyl ester 5-(2-thiophen-2-yl-ethyl) ester 
• 107610-35-5 2-Hydroxy-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-[1-(4-fluoro-benzyl)-piperidin-3-yl] ester 3-methyl ester 
• 107610-46-8 2-Chloro-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-[1-(4-fluoro-benzyl)-piperidin-3-yl] ester 3-methyl ester 
• 107610-30-0 5-[2-(4-benzhydrylpiperazin-1-yl)ethyl]oxycarbonyl-2-hydroxy-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine 
• 22985-44-0 2-nitro-3-(3-nitro-phenyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester 
• 857803-36-2 bromo-(3,α'-dinitro-bibenzyl-α-yl)-malonic acid dimethyl ester 

Relevant articles and documents

Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates

A method has been developed for the synthesis of substituted β-styrylmalonates by conversion of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) in the presence of gallium trichloride into the corresponding- 1,2-zwitterionic intermediates or (2-arylethyl-idene)malonates, followed by treatment with pyridine at room temperature leading to an isomerization of the emerging double bond. This method allows one to expand these reactions to include ACDCs with acceptor substituents at the aromatic ring.

GaCl3-Mediated "inverted" Formal [3 + 2]-Cycloaddition of Donor-Acceptor Cyclopropanes to Allylic Systems

A new process of "inverted" formal [3 + 2]-cycloaddition of donor-acceptor cyclopropanes (DACs) to allylic systems to give polyfunctionalized cyclopentanes has been developed. Unlike the classical version of formal [3 + 2]-cycloaddition, a DAC acts in thi

Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors

Inhibition of TLR4 signaling is an important therapeutic strategy for intervention in the etiology of several pro-inflammatory diseases. There has been intensive research in recent years aiming to explore this strategy, and identify small molecule inhibitors of the TLR4 pathway. However, the recent failure of a number of advanced drug candidates targeting TLR4 signaling (e.g., TAK242 and Eritoran) prompted us to continue the search for novel chemical scaffolds to inhibit this critical inflammatory response pathway. Here we report the identification of a group of new TLR4 signaling inhibitors through a cell-based screening. A series of arylidene malonate analogs were synthesized and assayed in murine macrophages for their inhibitory activity against LPS-induced nitric oxide (NO) production. The lead compound 1 (NCI126224) was found to suppress LPS-induced production of nuclear factor-kappaB (NF-κB), tumor necrosis factor (TNF-α), interleukin-1β (IL-1β), and nitric oxide (NO) in the nanomolar-low micromolar range. Taken together, this study demonstrates that 1 is a promising potential therapeutic candidate for various inflammatory diseases.