3377-20-6

Basic information

• Product Name: diethyl methylidenemalonate
• Synonyms: diethyl methylidenemalonate;Diethyl 2-methylenemalonate;Diethyl ethylene-1,1-dicarboxylate;Diethyl methylenemalonate;Methylenemalonic acid diethyl ester;Methylenepropanedioic acid diethyl ester;Propanedioic acid, 2-Methylene-, 1,3-diethyl ester;Propanedioic acid,2-Methylene-, 1,3-diethyl este
• CAS NO: 3377-20-6
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• Mol File: 3377-20-6.mol
• Article Data: 20

Chemical Properties

• Melting Point: 135.5-136.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 174.4°Cat760mmHg
• Flash Point: 73°C
• Appearance: /
• Density: 1.059g/cm³
• Vapor Pressure: 1.21mmHg at 25°C
• Refractive Index: 1.433
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: diethyl methylidenemalonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl methylidenemalonate(3377-20-6)
• EPA Substance Registry System: diethyl methylidenemalonate(3377-20-6)

Safety Data

• Hazardous Substances Data: 3377-20-6(Hazardous Substances Data)

Usage

Description

Diethyl methylidenemalonate, also known as diethyl 2-methylenemalonate, is an organic compound that serves as a versatile reagent in the synthesis of various chemical compounds. It is characterized by its ability to participate in [2+2] cycloaddition reactions, making it a valuable component in the field of organic chemistry.

Uses

Used in Chemical Synthesis:
Diethyl methylidenemalonate is used as a reagent for synthesizing donor-acceptor cyclobutanes. This application is made possible due to its ability to undergo [2+2] cycloaddition reactions when catalyzed by copper acetate or iron trichloride. The resulting cyclobutanes have potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C8H12O4/c1-4-11-7(9)6(3)8(10)12-5-2/h3-5H2,1-2H3

Upstream product

• 996-82-7 sodium diethylmalonate 
• 107-30-2 chloromethyl methyl ether 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 116279-89-1 9,10-dihydro-9,10-ethano-anthracene-11,11-dicarboxylic acid diethyl ester 
• 64-17-5 ethanol 
• 58567-05-8 diethyl 2-hydroxy-2-methylmalonate 
• 105-53-3 diethyl malonate 
• 50-00-0 formaldehyd 
• 609-09-6 Diethyl ketomalonate 
• 609-08-5 Diethyl methylmalonate 
• 20605-01-0 diethyl bis(hydroxymethyl)malonate 
• 141085-35-0 C₃H₈N⁽¹⁺⁾*C₂H₃O₂^(1-) 
• 1161393-21-0 thymidine 5'-bis[3-acetyloxymethoxy-2,2-bis(ethoxycarbonyl)-propyl]phosphate 
• 1161393-20-9 thymidine 5'-bis[3-acetyloxy-2,2-bis(ethoxycarbonyl)propyl]phosphate 

Downstream Products

• 854723-35-6 2,2,4-trimethyl-cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester 
• 38511-09-0 cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester 
• 4504-11-4 (N-hydroxy-anilinomethylene)-malonic acid diethyl ester 
• 2698-65-9 4-methylcyclohex-3-ene-1,1-dicarboxylic acid diethyl ester 
• 74555-31-0 2,3-diphenyl-isoxazolidine-4,4-dicarboxylic acid diethyl ester 
• 31696-00-1 diethyl 2-(3-butenyl)malonate 
• 55704-60-4 4-oxo-cyclohexane-1,1-dicarboxylic acid diethyl ester 
• 894778-80-4 (RS)-2-[(1-benzyloxycarbonylamino-2-phenyl-ethyl)-hydroxy-phosphinoylmethyl]-malonic acid diethyl ester 

Relevant articles and documents

COMPOUNDS FOR SELECTIVE BINDING TO ESTROGEN RECEPTORS ALPHA/BETA RELATIVE TO GPER/GPR30

The current invention is in the field of molecular biology/pharmacology and provides novel 3-oxabicyclo [3.3.1] nonene compounds and derivatives that modulate the effects of the classical estrogen receptors alpha and beta (ERalpha and ERbeta) with little to no biological or physiological effects on the G protein-coupled estrogen receptor GPER (also known as GPR30). These compounds may function as agonists and/or antagonists of one or more of the disclosed classical estrogen receptors.

Development of a Scalable Process for the Insecticidal Candidate Tyclopyrazoflor. Part 1. Evaluation of [3 + 2] Cyclization Strategies to 3-(3-Chloro-1 H-pyrazol-1-yl)pyridine

The evaluation of [3 + 2] cyclization strategies to prepare a key intermediate, 3-(3-chloro-1H-pyrazol-1-yl)pyridine, for the insecticidal candidate tyclopyrazoflor (1) is described. Among the validated strategies, the route involving [3 + 2] cyclization of 3-hydrazinopyridine·2HCl with methyl acrylate was selected for further optimization. This route provided ready access to 3-(3-chloro-1H-pyrazol-1-yl)pyridine in three steps via cyclization, chlorination, and oxidation. Further functionalization of 3-(3-chloro-1H-pyrazol-1-yl)pyridine via nitration, reduction, and amide formation with 3-((3,3,3-trifluoropropyl)thio)propanoic acid followed by ethylation rendered 1 in a total of seven steps.

[1+1+3] Annulation of Diazoenals and Vinyl Azides: Direct Synthesis of Functionalized 1-Pyrrolines through Olefination

A dirhodium carboxylate catalyzed [1+1+3] annulation reaction of diazoenals and vinyl azides that gives synthetically important enal-functionalized 1-pyrroline derivatives was developed. The reaction involves a novel rhodium-catalyzed olefination of diazoenals with vinyl azides via electrophilic enal carbenoids, resulting in a new class of enal acrylates. The annulation reaction was used for the direct synthesis of valuable deuterated 1-pyrrolines. Structural diversification of the enal-functionalized 1-pyrrolines resulted in the biologically important pyrrolidine-fused oxaziridine, amino acid derivatives, and a 6-azabicyclo[3.2.1]octane motif present in polycyclic alkaloids.