3377-21-7

Basic information

• Product Name: dimethyl methylenemalonate
• Synonyms: dimethyl methylenemalonate;Dimethyl ethylene-1,1-dicarboxylate;Methylenemalonic acid dimethyl ester;Methylenepropanedioic acid dimethyl ester;Einecs 222-171-2;Propanedioic acid, 2-Methylene-, 1,3-diMethyl ester
• CAS NO: 3377-21-7
• Molecular Formula: C6H8O4
• Molecular Weight: 144.12532
• EINECS: 222-171-2
• Mol File: 3377-21-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 126.5°Cat760mmHg
• Flash Point: 49.6°C
• Appearance: /
• Density: 1.113g/cm³
• Vapor Pressure: 11.6mmHg at 25°C
• Refractive Index: 1.423
• CAS DataBase Reference: dimethyl methylenemalonate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl methylenemalonate(3377-21-7)
• EPA Substance Registry System: dimethyl methylenemalonate(3377-21-7)

Safety Data

• Hazardous Substances Data: 3377-21-7(Hazardous Substances Data)

Usage

General Description

Dimethyl methylenemalonate is a chemical compound with the molecular formula C7H10O4. It is a colorless liquid with a fruity odor, commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Dimethyl methylenemalonate is known for its ability to undergo a variety of chemical reactions, including esterification, alkylation, and condensation. Its versatile reactivity and stability make it an important building block for the production of complex organic molecules. In addition, it is commonly used as a reagent in organic synthesis and is also employed as a solvent in various chemical processes. However, it is important to handle dimethyl methylenemalonate with caution, as it is flammable and can pose safety hazards if not properly managed.

InChI:InChI=1/C6H8O4/c1-4(5(7)9-2)6(8)10-3/h1H2,2-3H3

Upstream product

• 64-19-7 acetic acid 
• 108-59-8 malonic acid dimethyl ester 
• 50-00-0 formaldehyd 
• 3298-40-6 mesoxalate de methyle 
• 6773-29-1 dimethyl diazomalonate 
• 33757-46-9 8-(N-propionylamino)quinoline 
• 628-51-3 diacetoxymethane 
• 1338951-12-4 dimethyl 3,3-dimethyl-2-(diphenylmethylideneamino)cyclobutane-1,1-dicarboxylate 
• 609-02-9 methyl-malonic acid dimethylester 
• 116279-88-0 11,11-bis(methoxycarbonyl)-9,10-endoethano-9,10-dihydroanthracene 
• 87167-72-4 dimethyl 2-methyl-2-phenylselenopropanedioate 
• 60-29-7 diethyl ether 
• 2373-51-5 chloro-methylsulfanyl-methane 

Downstream Products

• 13138-07-3 (5-phenyl-2-thioxo-[1,3,4]oxadiazol-3-ylmethyl)-malonic acid dimethyl ester 
• 17819-17-9 2-methoxy-3-(4-nitro-phenyl)-isoxazolidine-5,5-dicarboxylic acid dimethyl ester 
• 51013-62-8 3-phenyl-4H-isoxazole-5,5-dicarboxylic acid dimethyl ester 
• 94473-56-0 1-benzyl-4,4-bis(methoxycarbonyl)-4,5-dihydro-1,2,3-triazole 
• 96914-60-2 dimethyl 2-(cyclohex-1-en-1-yl)cyclopropane-1,1-dicarboxylate 
• 217654-79-0 2-cyclohexylmethyl-malonic acid dimethyl ester 
• 82167-55-3 3,4-Bis-trimethylsilanylmethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester 
• 78465-00-6 Oxiran-1,1-dicarbonsaeure-dimethylester 
• 951214-92-9 C₁₅H₁₉NO₆ 
• 17819-20-4 1,1-Dicarbomethoxy-1-hydroxy-3-methoximino-3-phenylpropan 
• 17819-21-5 1,1-Dicarbomethoxy-1-hydroxy-3-methoximino-3-p-nitrophenylpropan 
• 109432-97-5 4,4-dicarbomethoxy-1,2-dimethylene cyclohexane 

Relevant articles and documents

Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3- carboxylates and 3-carbonitriles

Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3- carbonitriles were obtained in a one-flask reaction.

Total Synthesis of the Meroterpenoid Manginoid A as Fueled by a Challenging Pinacol Coupling and Bicycle-forming Etherification

The manginoids are a unique collection of bioactive natural products whose structures fuse an oxa-bridged spirocyclohexanedione with a heavily substituted trans-hydrindane framework. Herein, we show that such architectures can be accessed through a strategy combining a challenging pinacol coupling and bicycle-forming etherification with several additional chemo- and regioselective reactions. The success of these key events proved to be highly substrate and condition specific, affording insights for their application to other targets. As a result, not only has a 19-step total synthesis of manginoid A been achieved, but a potential roadmap to access other members of the family and related natural products has also been identified.

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Three-Dimensional Tetrathiafulvalene-Based Covalent Organic Frameworks for Tunable Electrical Conductivity

The functionalization of three-dimensional (3D) covalent organic frameworks (COFs) is essential to broaden their applications. However, the introduction of organic groups with electroactive abilities into 3D COFs is still very limited. Herein we report the first case of 3D tetrathiafulvalene-based COFs (3D-TTF-COFs) with non- or 2-fold interpenetrated pts topology and tunable electrochemical activity. The obtained COFs show high crystallinity, permanent porosity, and large specific surface area (up to 3000 m2/g). Furthermore, these TTF-based COFs are redox active to form organic salts that exhibit tunable electric conductivity (as high as 1.4 × 10-2 S cm-1 at 120 °C) by iodine doping. These results open a way toward designing 3D electroactive COF materials and promote their applications in molecular electronics and energy storage.