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

Description

[(4-Chlorophenyl)methylene]malonic acid diethyl ester is a chemical compound characterized by the molecular formula C14H15ClO4. It is a diethyl ester derivative of malonic acid, featuring a 4-chlorophenyl group connected to the malonic acid via a methylene bridge. [(4-Chlorophenyl)methylene]malonic acid diethyl ester is known for its utility in organic synthesis and its role as a building block in the creation of pharmaceutical drugs and agrochemicals. However, due to the presence of the 4-chlorophenyl group, it is considered potentially toxic and requires careful handling.

Uses

Used in Organic Synthesis:
[(4-Chlorophenyl)methylene]malonic acid diethyl ester serves as a reagent in organic synthesis, facilitating the preparation of a variety of organic compounds. Its unique structure allows for versatile reactions and the formation of diverse chemical products.
Used in Pharmaceutical Drug Synthesis:
In the pharmaceutical industry, [(4-Chlorophenyl)methylene]malonic acid diethyl ester is utilized as a key building block for the synthesis of drugs. Its incorporation into drug molecules can contribute to the development of new therapeutic agents with specific pharmacological properties.
Used in Agrochemical Synthesis:
Similarly, in agrochemical applications, this compound is employed in the synthesis of various agrochemicals. Its structural features can be leveraged to create compounds with pesticidal or herbicidal activity, contributing to agricultural productivity and crop protection.

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.

Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds

An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.

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.