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

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

Uses

Used in Organic Synthesis:
2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER is used as a reagent for the synthesis of various organic compounds, leveraging its unique structural features to facilitate chemical reactions and form new molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER is utilized as a key intermediate in the development of pharmaceuticals. Its properties allow it to be incorporated into drug molecules, potentially enhancing their therapeutic effects.
Used in Pharmaceutical Industry:
2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER is used as a building block in the creation of new pharmaceuticals, contributing to the discovery and synthesis of novel drug candidates for various medical conditions.
Used in Agrochemical Industry:
2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER is also used as a reagent in the synthesis of agrochemicals, such as pesticides and herbicides, where its chemical properties can be harnessed to develop more effective and targeted products for agricultural use.

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

Upstream product

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

Downstream Products

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

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.

Simple access to highly functional bicyclic γ- and δ-lactams: Origins of chirality transfer to contiguous tertiary/quaternary stereocenters assessed by DFT

This paper describes the synthesis of both polysubstituted oxazolo-pyrrolidinones and -piperidinones by a domino process. The methodology is based on the reaction between hydroxyl halogenoamides and Michael acceptors, which leads efficiently to bicyclic lactams. The process is compatible with unsymmetrical electron-withdrawing groups on the Michael acceptor, which allows the formation of two contiguous and fully controlled tertiary and quaternary stereocenters. In the case of tetrasubstituted Michael acceptors, two adjacent quaternary stereocenters are formed in good yield. Starting from (R)-phenylglycinol derived amides results in the formation of enantioenriched bicyclic lactams in low to good yields and with high levels of stereo-selectivity, thus greatly increasing the scope and interest of this strategy. The origins of chirality transfer and diastereoselectivity were studied by DFT calculations and have been attributed to a kinetic control in one of the last two steps of the reaction sequence. This selectivity is dependent upon both the substituents on the Michael acceptor and the sodium cation chelation.

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.