28783-51-9

Basic information

• Product Name: 2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER
• Synonyms: 2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER;Propanedioic acid, 2-(chloromethylene)-, 1,3-diethyl ester;Diethyl 2-(chloromethylene)malonate
• CAS NO: 28783-51-9
• Molecular Formula: C₈H₁₁ClO₄
• Molecular Weight: 206.62
• Mol File: 28783-51-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 210.5 °C at 760 mmHg
• Flash Point: 74 °C
• Appearance: /
• Density: 1.198 g/cm³
• Vapor Pressure: 0.192mmHg at 25°C
• Refractive Index: 1.462
• CAS DataBase Reference: 2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER(28783-51-9)
• EPA Substance Registry System: 2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER(28783-51-9)

Safety Data

• Hazardous Substances Data: 28783-51-9(Hazardous Substances Data)

Usage

General Description

2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER is a chemical compound that is used in organic synthesis and medicinal chemistry. It is a diethyl ester derivative of malonic acid, containing a chloromethylene group. 2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER is commonly used as a reagent in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. It is a colorless liquid with a slightly fruity odor, and it is typically handled and stored under inert gas to prevent degradation. The compound is also known to be toxic and should be handled with care in a laboratory setting.

InChI:InChI=1/C8H11ClO4/c1-3-12-7(10)6(5-9)8(11)13-4-2/h5H,3-4H2,1-2H3

Upstream product

• 626-10-8 chloro-maleic acid diethyl ester 
• 33142-25-5 diethyl α-formylmalonate 
• 20734-18-3 diethyl 2-(hydroxymethylene)malonate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 6768-23-6 diethyl-2-(4-methoxybenzylidene)malonate 
• 14111-33-2 diethyl 2-(4-methylbenzylidene)malonate 
• 40131-09-7 diethyl methoxymethylenemalonate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 188760-98-7 2-Benzyloxymethylene-malonic acid diethyl ester 
• 188761-03-7 2-(Bis-benzyloxy-methyl)-malonic acid diethyl ester 
• 70358-02-0 2-phenoxymethylene-malonic acid diethyl ester 
• 5932-27-4 ethyl 1H-pyrazole-3-carboxylate 

Relevant articles and documents

Free-Radical Carbo-Alkenylation of Olefins: Scope, Limitations and Mechanistic Insights

The three-component free-radical carbo-alkenylation of electron-rich olefins has been studied, varying the substitution pattern in the alkene, in the radical precursor and in the final acceptor. New vinylsulfones were also prepared and their reactivity investigated. The scope and limitations of the process was established, and the reaction mechanism clarified using selected dienes as radical clocks. It was thus recognised that the reversible addition onto the olefin of the released sulfonyl group is an important event, which should not be overlooked when using such multicomponent carbo-alkenylation reactions.

Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxyl-2-hydroxymethylpropanal acetals

Prochiral dialkylacetal derivatives of 3-hydroxy-2-hydroxymethylpropanal 6a-e were synthesized from the corresponding 2-substituted diethyl malonates 5a-e and subjected to asymmetric enzymatic acetylation. The diethyl malonates 5a-f were prepared from diethyl chloromethylenemalonate 3 by using either a one- or a two-step process. Asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal diethyl acetal 6b with several enzymes was studied first, showing the highest enantiotopic selectivity with lipase from Pseudomonas fluorescens (PFL). Solvent effect was also investigated: the best selectivity was obtained in a mixture of hexane and diethyl ether. Furthermore, several other acetals 6a-e were also tested under the optimal acetylation conditions.