Dimethyl allylmalonate

Base Information

• Chemical Name: Dimethyl allylmalonate
• CAS No.: 40637-56-7
• Molecular Formula: C8H12O4
• Molecular Weight: 172.181
• Hs Code.: 2917190090
• European Community (EC) Number: 255-017-8
• DSSTox Substance ID: DTXSID40193642
• Nikkaji Number: J113.153B
• Wikidata: Q72468801
• Mol file: 40637-56-7.mol

Synonyms:Dimethyl allylmalonate;40637-56-7;Dimethyl 2-allylmalonate;dimethyl 2-prop-2-enylpropanedioate;Propanedioic acid, 2-propenyl-, dimethyl ester;EINECS 255-017-8;MFCD00014959;1,3-dimethyl 2-(prop-2-en-1-yl)propanedioate;Dimethyl2-allylmalonate;Dimethyl 2-allylmalonate #;Dimethyl allylmalonate, 98%;SCHEMBL452544;DTXSID40193642;AKOS005206818;CS-W017611;2-allyl-propanedioic acid dimethyl ester;AS-12604;SY061996;FT-0622050;FT-0625036;prop-2-enyl-propanedioic acid dimethyl ester;EN300-123355;A825209;dimethyl 2-allylpropanedioate;J-802194

Chemical Property of Dimethyl allylmalonate

Chemical Property:

• Vapor Pressure: 1.89mmHg at 25°C
• Melting Point: <-80 °C
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 165.239 °C at 760 mmHg
• PKA: 12.58±0.46(Predicted)
• Flash Point: 67.259 °C
• PSA: 52.60000
• Density: 1.056 g/cm³
• LogP: 0.52470
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl allylmalonate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 23-24/25-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(CC=C)C(=O)OC
• Uses: Dimethyl allylmalonate is used as an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs.

Technology Process of Dimethyl allylmalonate

There total 40 articles about Dimethyl allylmalonate 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 acetate (591-87-7) + malonic acid dimethyl ester (108-59-8) → dimethyl allylmalonate (40637-56-7)

Guidance literature:

With triphenylphosphine mono-sulfonate; tert-butylimino-tri(pyrrolidino)phosphorane; palladium diacetate; In diethyl ether; hexane; for 6h; Heating; 0.2 ppm Pd leaching;

DOI:10.1016/S0040-4039(97)00890-3

Reference yield: 97.0%

dimethyl (prop-2-yn-1-yl)malonate (95124-07-5) → dimethyl allylmalonate (40637-56-7)

Guidance literature:

With sodium dodecylbenzenesulfonate; hydrogen; palladium diacetate; In water; at 25 ℃; for 1.5h; under 760.051 Torr;

DOI:10.1021/acs.joc.8b00314

Reference yield: 94.0%

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

Guidance literature:

malonic acid dimethyl ester; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

allyl bromide; for 15h; Heating;

DOI:10.1016/S0040-4039(02)02594-7

upstream raw materials:

methanol

allylmalonic acid

buta-1,3-diene

acetylacetone

Downstream raw materials:

dimethyl 4-oxocyclopent-2-enyl(allyl)malonate

dihydro-3-carbomethoxy-5-<(phenylseleno)methyl>-2(3H)-furanone

7-(cyclohex-1-en-1-yl)-4,4-bis(methoxycarbonyl)-1,6-heptadiene

trans-dimethyl 2-(4-acetoxycyclohex-2-enyl)-2-(prop-2-enyl)propanedioate

Refernces

• 1、 Abbasi Kejani, Alireza,Khosravi, Hormoz,Rominger, Frank,Balalaie, Saeed,Breit, Bernhard. "Metal-Free Domino Oligocyclization Reactions of Enynals and Enynones with Molecular Oxygen". supporting information. p. 1291 - 1295. Retrieved 2021/02/20.
• 2、 Tappin, Nicholas D. C.,Renaud, Philippe. "Methyl Radical Initiated Kharasch and Related Reactions". supporting information. p. 275 - 282. Retrieved 2020/12/07.