10565-13-6

Basic information

• Product Name: DIETHYL 4-NITROPHENYL MALONATE
• Synonyms: RARECHEM AL BI 1252;DIETHYL 2-(4-NITROPHENYL)MALONATE;DIETHYL 4-NITROPHENYL MALONATE;2-(4-Nitrophenyl)-malonic acid diethylester;Diethyl 2-(p-nitrophenyl)malonate
• CAS NO: 10565-13-6
• Molecular Formula: C₁₃H₁₅NO₆
• Molecular Weight: 281.26
• Mol File: 10565-13-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 58-59℃
• Boiling Point: 381.1 °C at 760 mmHg
• Flash Point: 154.1 °C
• Appearance: /
• Density: 1.253 g/cm³
• CAS DataBase Reference: DIETHYL 4-NITROPHENYL MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 4-NITROPHENYL MALONATE(10565-13-6)
• EPA Substance Registry System: DIETHYL 4-NITROPHENYL MALONATE(10565-13-6)

Safety Data

• Hazardous Substances Data: 10565-13-6(Hazardous Substances Data)

Usage

General Description

DIETHYL 4-NITROPHENYL MALONATE is a yellow to orange crystalline compound used as an intermediate in the synthesis of pharmaceuticals and organic compounds. It is a malonic acid derivative that contains two ethyl groups, a 4-nitrophenyl group, and a carboxylate group. It is commonly used as a reagent in organic chemical reactions, such as the Claisen condensation, to form a wide variety of carbon-carbon bonds. Additionally, it has potential applications in the development of agrochemicals and as a precursor for the synthesis of dyes and pigments. However, it should be handled with caution as it is toxic if ingested or inhaled and may cause skin and eye irritation.

Upstream product

• 5445-26-1 ETHYL 4-NITROPHENYLACETATE 
• 623-49-4 ethyl cyanoformate 
• 636-98-6 p-nitrobenzene iodide 
• 105-53-3 diethyl malonate 
• 100-00-5 4-chlorobenzonitrile 
• 350-46-9 4-Fluoronitrobenzene 
• 50434-36-1 4-nitrophenylacetyl chloride 
• 104-03-0 4-nitrobenzeneacetic acid 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 57337-91-4 diethyl 2-<(methylsulfonyl)oxy>-2-(p-nitrophenyl)ethylene-1,1-dicarboxylate 
• 119350-25-3 3,5-dihydroxy-4-(p-nitrophenyl)pyrazole 
• 1241599-62-1 N-p-tolylsulfonyl-2,2-bis(ethoxycarbonyl)-2-(4-nitrophenyl)acetamide 
• 1068582-76-2 (4-nitrophenyl)(ethoxycarbonyl)acetic acid N-(ethoxycarbonyl)-N-phenylamide 
• 1785-02-0 triphenyl isocyanurate 
• 58007-22-0 2-(2,4-dimethoxy-benzylidene)-4-(4-nitro-phenyl)-3,5-dioxo-isoxazolidinium betaine 
• 58007-26-4 2-(4-hydroxy-3-methoxy-benzylidene)-4-(4-nitro-phenyl)-3,5-dioxo-isoxazolidinium betaine 
• 58007-21-9 2-(4-dimethylamino-benzylidene)-4-(4-nitro-phenyl)-3,5-dioxo-isoxazolidinium betaine 
• 58007-23-1 2-(4-methoxy-benzylidene)-4-(4-nitro-phenyl)-3,5-dioxo-isoxazolidinium betaine 
• 58007-25-3 2-(4-chloro-benzylidene)-4-(4-nitro-phenyl)-3,5-dioxo-isoxazolidinium betaine 
• 58007-27-5 2-benzylidene-4-(4-nitro-phenyl)-3,5-dioxo-isoxazolidinium betaine 
• 58007-45-7 2-(1,1-dimethyl-3-oxo-butyl)-4-(4-nitro-phenyl)-isoxazolidine-3,5-dione 
• 79815-61-5 anhydro-5,7-dimethyl-1-hydroxy-2-(4-nitrophenyl)-3-oxopyrazolo<1,2-a>pyrazolium hydroxide 
• 79815-60-4 C₁₃H₉N₃O₄ 

Relevant articles and documents

Copper(I) Iodide-Catalyzed (Het)arylation of Diethyl Malonate with (Het)aryl Bromides by Using 1,3-Benzoxazole as a Ligand

An efficient Ullmann-type coupling of aryl bromides with diethyl malonate in the presence of copper(I) iodide and 1,3-benzoxazole is presented. This method has a broad substrate scope (heterocyclic and phenyl bromides) and good functional-group tolerance (OMe, Me, Ac, CN, NO 2, F, and Cl). Moreover, less time is needed to reach full conversion (3-9 hours).

First heterogeneously palladium catalysed α-arylation of diethyl malonate

Pd exchanged NaY zeolites ([Pd(0)]-, [Pd(II)]- and entrapped [Pd(NH3)4]) exhibit a good activity towards the α-arylation of carbonyl compounds using different para-substituted aryl bromides. Low Pd-concentrations (only 2 mol%) are required to observe interesting activity. The catalysts can easily be separated from the reaction mixture and reused without any loss in activity. For large-scale applications the alternative use of an insoluble base as K2CO3 seems to be promising. The electronic nature of the aryl halides plays a limited role concerning the rate of the reaction.

Nucleophilic Reactivities of 2-Substituted Malonates

Kinetics of the reactions of 2-substituted malonate anions and 5-substituted Meldrum's acid anions with benzhydrylium ions and structurally related quinone methides have been monitored in dimethyl sulfoxide solution at 20 °C. The resulting second-order rate constants followed the correlation lg k(20 °C) = sN(E + N), which allowed the nucleophile-specific parameters N and sN to be calculated for these highly stabilized carbanions and to integrate them in our comprehensive nucleophilicity scale. Given that the reactions of the benzhydrylium ions with the anions derived from 5-aryl-substituted Meldrum's acids did not proceed to completion, the corresponding equilibrium constants could be determined. In combination with available data for pyridines and benzoate ions, these equilibrium constants provide a direct comparison of the strengths of C-, N-, and O-centered Lewis bases with respect to C-centered Lewis acids.

NAMPT MODULATORS

Provided are compounds of Formula (II) or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, and p are as defined herein. Also provided is a pharmaceutically acceptable composition comprising a compound of Formula (II), or a pharmaceutically acceptable salt thereof. Also provided are methods of using a compound of Formula (II), or a pharmaceutically acceptable salt thereof.

Method for immobilizing CuI to catalyze active methylene compound arylation by adopting fixed bed microchannel reaction device

The invention discloses a method for immobilizing CuI to catalyze active methylene compound arylation by adopting a fixed bed microchannel reaction device. The method comprises the steps of (1) dissolving aryl halide ArX into a first organic solvent; (2) dissolving an active methylene compound, a nitrogen-oxygen polydentate ligand and organic alkali into a second organic solvent; (3) adding a solid catalyst copper iodide to a fixed bed microstructure reactor in the fixed bed microchannel reaction device; and (4) mixing the solution obtained in the step (1) and the solution obtained in the step (2) in a mixer of the microchannel reaction device, pumping the mixed solution into the fixed bed microstructure reactor obtained in the step (3), and collecting an outflow liquid after reaction. The used catalyst and ligand are low in price and easily available. Compared with the same type of reaction in the prior art, the method is short in reaction time and mild in reaction condition and has good application prospect.