Dimethyl methylenemalonate

Base Information

• Chemical Name: Dimethyl methylenemalonate
• CAS No.: 3377-21-7
• Molecular Formula: C6H8 O4
• Molecular Weight: 144.127
• Hs Code.: 2917190090
• European Community (EC) Number: 222-171-2
• UNII: YQN34UG3PK
• DSSTox Substance ID: DTXSID30187434
• Nikkaji Number: J121.397K
• Wikidata: Q83059141
• Mol file: 3377-21-7.mol

Synonyms:Dimethyl methylenemalonate;3377-21-7;Dimethyl 2-methylenemalonate;dimethyl 2-methylidenepropanedioate;YQN34UG3PK;Propanedioic acid, methylene-, dimethyl ester;EINECS 222-171-2;Methylenemalonic acid, dimethyl ester;dimethyl methlenemalonate;UNII-YQN34UG3PK;Dimethyl2-methylenemalonate;SCHEMBL40660;Methylenmalonsauredimethylester;Dimethyl 2-methylenemalonate #;DTXSID30187434;2-METHYLENE DIMETHYL MALONATE;AKOS015917407;1,3-DIMETHYL 2-METHYLIDENEPROPANEDIOATE;Propanedioic acid, 2-methylene-, 1,3-dimethyl ester

Chemical Property of Dimethyl methylenemalonate

Chemical Property:

• Vapor Pressure: 11.6mmHg at 25°C
• Boiling Point: 126.5°Cat760mmHg
• Flash Point: 49.6°C
• PSA: 52.60000
• Density: 1.113g/cm³
• LogP: -0.11140
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=C)C(=O)OC

Technology Process of Dimethyl methylenemalonate

There total 13 articles about Dimethyl methylenemalonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-methylenemalonate (3377-21-7)

Guidance literature:

With trifluoroacetic acid; diisopropylamine 2,2,2-trifluoroacetic acid salt; In tetrahydrofuran; for 8h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201303803

Reference yield: 54.0%

11,11-bis(methoxycarbonyl)-9,10-endoethano-9,10-dihydroanthracene (116279-88-0) → dimethyl 2-methylenemalonate (3377-21-7)

Guidance literature:

With maleic anhydride; In paraffin; at 225 ℃; for 0.75h;

DOI:10.1021/jo00255a038

Reference yield: 50.0%

malonic acid dimethyl ester (108-59-8) → dimethyl 2-methylenemalonate (3377-21-7)

Guidance literature:

With PRIMENE 81-R iminium-MSA; at 100 ℃; for 0.0166667h; Neat (no solvent);

upstream raw materials:

formaldehyd

malonic acid dimethyl ester

diethyl ether

chloro-methylsulfanyl-methane

Downstream raw materials:

(5-phenyl-2-thioxo-[1,3,4]oxadiazol-3-ylmethyl)-malonic acid dimethyl ester

2-methoxy-3-(4-nitro-phenyl)-isoxazolidine-5,5-dicarboxylic acid dimethyl ester

1-benzyl-4,4-bis(methoxycarbonyl)-4,5-dihydro-1,2,3-triazole

dimethyl 2-(cyclohex-1-en-1-yl)cyclopropane-1,1-dicarboxylate

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