Dimethyl diallylmalonate

Base Information

• Chemical Name: Dimethyl diallylmalonate
• CAS No.: 35357-77-8
• Molecular Formula: C11H16O4
• Molecular Weight: 212.246
• Hs Code.: 2917190090
• European Community (EC) Number: 252-526-7
• UNII: BJO8IH9097
• DSSTox Substance ID: DTXSID80188850
• Nikkaji Number: J260.598H
• Wikidata: Q83060703
• Mol file: 35357-77-8.mol

Synonyms:Dimethyl diallylmalonate;35357-77-8;dimethyl 2,2-diallylmalonate;dimethyl 2,2-bis(prop-2-enyl)propanedioate;BJO8IH9097;EINECS 252-526-7;UNII-BJO8IH9097;dimethyl diallyl malonate;SCHEMBL770755;diallylmalonic acid dimethyl ester;DTXSID80188850;FT-0625039;FT-0625129;4,4-BIS(CARBOMETHOXY)-1,6-HEPTADIENE;DI-2-PROPENYLPROPANEDIOIC ACID DIMETHYL ESTER;PROPANEDIOIC ACID, 2,2-DI-2-PROPEN-1-YL-, 1,3-DIMETHYL ESTER

Chemical Property of Dimethyl diallylmalonate

Chemical Property:

• Vapor Pressure: 0.00672mmHg at 25°C
• Refractive Index: 1.452
• Boiling Point: 209.7 °C at 760 mmHg
• Flash Point: 87.2 °C
• PSA: 52.60000
• Density: 1.023 g/cm³
• LogP: 1.47100
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 212.10485899
• Heavy Atom Count: 15
• Complexity: 240

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Dimethyl diallylmalonate

There total 27 articles about Dimethyl diallylmalonate 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: 98.0%

allyl bromide (106-95-6) + malonic acid dimethyl ester (108-59-8) → dimethyl bisallylmalonate (35357-77-8)

Guidance literature:

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

allyl bromide; In tetrahydrofuran; mineral oil; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo3015209

Reference yield: 87.0%

allyl bromide (106-95-6) + malonic acid dimethyl ester (108-59-8) → dimethyl allylmalonate (40637-56-7) + dimethyl bisallylmalonate (35357-77-8)

Guidance literature:

With potassium carbonate; In water; acetone; at 0 - 30 ℃;

DOI:10.1002/adsc.202001000

Reference yield: 82.0%

allyl methyl carbonate (35466-83-2) + malonic acid dimethyl ester (108-59-8) → dimethyl bisallylmalonate (35357-77-8)

Guidance literature:

With triphenylphosphine; In water; at 120 ℃; for 1h;

DOI:10.1039/c7cc02380d

upstream raw materials:

methanol

2,2-diallylmalonic acid

tris(allyl)borate

dimethyl malonate sodium salt

Downstream raw materials:

methyl 3-(3-buten-1-yl)-4-p-toluenesulfonylmethyl-cyclopentane-1,1-dicarboxylate

methyl 3-chloromethyl-4-p-toluenesulfonylmethyl-cyclopentane-1,1-dicarboxylate

methyl 3-chloromethyl-4-p-toluenesulfonylmethyl-cyclopentane-1,1-dicarboxylate

methyl 3-(3-chloro-3-buten-1-yl)-4-p-toluenesulfonylmethyl-cyclopentane-1,1-dicarboxylate

Refernces

• 1、 Harrowven, David C.,May, Peter J.,Bradley, Mark. "Sulfur-mediated radical cyclisation reactions on solid support". . p. 503 - 506. Retrieved 2003.
• 2、 Stork, Gilbert,Mook, Robert. "FIVE VS SIX MEMBERED RING FORMATION IN THE VINYL RADICAL CYCLIZATION". . p. 4529 - 4532. Retrieved 1986.
• 3、 Tsuji, Jiro,Minami, Ichiro,Shimizu, Isao. "ALLYATION OF CARBONUCLEOPHILES WITH ALLYLIC CARBONATES UNDER NEUTRAL CONDITIONS CATALYZED BY RHODIUM COMPLEXES". . p. 5157 - 5160. Retrieved 1984.
• 4、 Sweeney, Joseph B.,Ball, Anthony K.,Smith, Luke J.. "Catalytic C?C Bond Formation Using a Simple Nickel Precatalyst System: Base- and Activator-Free Direct C-Allylation by Alcohols and Amines". supporting information. p. 7354 - 7357. Retrieved 2018/05/03.
• 5、 Llevot,Monney,Sehlinger,Behrens,Meier. "Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles". supporting information. p. 5175 - 5178. Retrieved 2017/07/12.