Dimethyl 2-allyl-2-(prop-2-yn-1-yl)malonate

Base Information

• Chemical Name: Dimethyl 2-allyl-2-(prop-2-yn-1-yl)malonate
• CAS No.: 107428-06-8
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• Hs Code.: 2917190090
• DSSTox Substance ID: DTXSID50446833
• Nikkaji Number: J1.037.656D
• Mol file: 107428-06-8.mol

Synonyms:Dimethyl 2-allyl-2-(prop-2-yn-1-yl)malonate;107428-06-8;dimethyl 2-prop-2-enyl-2-prop-2-ynylpropanedioate;Dimethyl2-allyl-2-(prop-2-yn-1-yl)malonate;DTXSID50446833;Allylpropargylmalonic acid dimethyl ester

Chemical Property of Dimethyl 2-allyl-2-(prop-2-yn-1-yl)malonate

Chemical Property:

• PSA: 52.60000
• LogP: 0.91820
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 292

Purity/Quality:

85.0-99.9% ^*data from raw suppliers

Dimethyl2-allyl-2-(prop-2-yn-1-yl)malonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Dimethyl 2-allyl-2-(prop-2-yn-1-yl)malonate

There total 3 articles about Dimethyl 2-allyl-2-(prop-2-yn-1-yl)malonate 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: 99.0%

dimethyl (prop-2-yn-1-yl)malonate (95124-07-5) + allyl bromide (106-95-6) → dimethyl allylpropargylmalonate (107428-06-8)

Guidance literature:

With potassium carbonate; In acetone; for 24h; Heating;

DOI:10.1021/ja00079a033

Reference yield: 98.0%

dimethyl allylmalonate (40637-56-7) + propargyl bromide (106-96-7) → dimethyl allylpropargylmalonate (107428-06-8)

Guidance literature:

dimethyl allylmalonate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;

propargyl bromide; In tetrahydrofuran; mineral oil; Inert atmosphere;

DOI:10.1002/anie.201204798

Reference yield:

malonic acid dimethyl ester (108-59-8) → dimethyl allylpropargylmalonate (107428-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

2.2: Inert atmosphere

With sodium hydride; In tetrahydrofuran; mineral oil;

DOI:10.1002/anie.201204798

upstream raw materials:

dimethyl (prop-2-yn-1-yl)malonate

allyl bromide

dimethyl allylmalonate

propargyl bromide

Downstream raw materials:

dimethyl 3,4-dimethylidenecyclopentane-1,1-dicarboxylate

3-methylene-cyclohexane-1,1-dicarboxylic acid dimethyl ester

3-methyl-4-methylene-cyclopentane-1,1-dicarboxylic acid dimethyl ester