6827-40-3

Basic information

• Product Name: [(4-Chlorophenyl)methylene]malonic acid diethyl ester
• Synonyms: (4-Chlorobenzylidene)malonic acid diethyl ester;[(4-Chlorophenyl)methylene]malonic acid diethyl ester;DIETHYL (4-CHLOROBENZYLIDENE)-MALONATE;Diethyl 2-(4-chlorobenzylidene)malonate
• CAS NO: 6827-40-3
• Molecular Formula: C₁₄H₁₅ClO₄
• Molecular Weight: 282.73
• Mol File: 6827-40-3.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 349.7°Cat760mmHg
• Flash Point: 129.7°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 4.61E-05mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C
• CAS DataBase Reference: [(4-Chlorophenyl)methylene]malonic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(4-Chlorophenyl)methylene]malonic acid diethyl ester(6827-40-3)
• EPA Substance Registry System: [(4-Chlorophenyl)methylene]malonic acid diethyl ester(6827-40-3)

Safety Data

• Hazardous Substances Data: 6827-40-3(Hazardous Substances Data)

Usage

General Description

[(4-Chlorophenyl)methylene]malonic acid diethyl ester is a chemical compound with the molecular formula C14H15ClO4. It is a diethyl ester derivative of malonic acid, containing a 4-chlorophenyl group linked to malonic acid through a methylene bridge. [(4-Chlorophenyl)methylene]malonic acid diethyl ester is commonly used in organic synthesis as a reagent for the preparation of various organic compounds. It is also used as a building block in the synthesis of pharmaceutical drugs and agrochemicals. The presence of the 4-chlorophenyl group makes this compound potentially toxic and should be handled with caution.

InChI:InChI=1/C14H15ClO4/c1-3-18-13(16)12(14(17)19-4-2)9-10-5-7-11(15)8-6-10/h5-9H,3-4H2,1-2H3

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 105-53-3 diethyl malonate 
• 631-22-1 diethyl dibromomalonate 
• 685-87-0 Diethyl 2-bromomalonate 
• 110-89-4 piperidine 
• 95-76-1 m,p-dichloroaniline 
• 37556-13-1 diethyl (4-chlorobenzyl)malonate 
• 104-86-9 4-chlorobenzylamine 

Downstream Products

• 40877-57-4 ethyl 3-(4-chlorophenyl)-3-cyanopropanoate 
• 22730-52-5 <α-(O,O-Diethyl-phosphono)-4-chlor-benzyl>-malonsaeure-diethylester 
• 22399-10-6 2-[(4-Chloro-phenyl)-(diethoxy-thiophosphorylsulfanyl)-methyl]-malonic acid diethyl ester 
• 74444-83-0 2-(4-chlorophenyl)cyclopropane-1,1-dicarboxylic acid diethyl ester 
• 37556-13-1 diethyl (4-chlorobenzyl)malonate 
• 6265-91-4 2-(4-chlorophenyl)benzothiazole 
• 72293-10-8 (2R,3S)-2-(4-Chloro-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepine-3-carboxylic acid ethyl ester 
• 87707-90-2 2-[(2-Amino-phenylsulfanyl)-(4-chloro-phenyl)-methyl]-malonic acid diethyl ester 
• 130944-14-8 ethyl 3-amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carboxylate 
• 130944-06-8 ethyl 2-amino-4-(4-chlorophenyl)-7-hydroxy-4H-chromene-3-carboxylate 
• 21980-09-6 (+/-)-p-Chlor-benzhydryl-malonsaeure-diethylester 
• 117553-57-8 Methanesulfonic acid (2R,3R)-2-(4-chloro-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylmethyl ester 
• 72293-11-9 (2S,3S)-2-(4-Chloro-phenyl)-3-hydroxymethyl-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 

Relevant articles and documents

Ball-Milling-Enabled Reactivity of Manganese Metal**

Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.

Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins

A highly environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives which attract interest due to their potential medicinal importance.

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.