Diethyl allylmalonate

Base Information

• Chemical Name: Diethyl allylmalonate
• CAS No.: 2049-80-1
• Deprecated CAS: 1347703-47-2
• Molecular Formula: C10H16O4
• Molecular Weight: 200.235
• Hs Code.: 2917.19
• European Community (EC) Number: 218-072-9
• NSC Number: 67393,8777
• UNII: M5ETZ38HUJ
• DSSTox Substance ID: DTXSID30883787
• Nikkaji Number: J26.303F
• Wikidata: Q72469053
• Mol file: 2049-80-1.mol

Synonyms:Diethyl allylmalonate;2049-80-1;Ethyl allylmalonate;Diethyl 2-allylmalonate;Allylmalonic acid diethyl ester;diethyl 2-prop-2-enylpropanedioate;Diethyl prop-2-enylpropanedioate;Diethyl 2-(prop-2-enyl)malonate;Malonic acid, allyl-, diethyl ester;Propanedioic acid, 2-propenyl-, diethyl ester;Propanedioic acid, 2-(2-propen-1-yl)-, 1,3-diethyl ester;NSC 8777;Diethyl 2-(2-propenyl)-1,3-propanedioate;1,3-diethyl 2-(prop-2-en-1-yl)propanedioate;NSC 67393;M5ETZ38HUJ;2-allylmalonic acid diethyl ester;NSC-8777;EINECS 218-072-9;MFCD00009155;NSC-67393;AI3-11069;Diethylallylmalonate;ALLYL MALONIC ACID;diethyl 2-allylpropanedioate;diethyl allyl-malonate;Diethyl-allyl-malonate;UNII-M5ETZ38HUJ;2-Allylmalonic acid diethyl;Diethyl allylmalonate, 95%;CBDivE_005373;SCHEMBL793641;Allylmalonic acid, diethyl ester;DTXSID30883787;NSC8777;2-Allyl-malonic acid diethyl ester;NSC67393;diethyl prop-2-en-1-ylpropanedioate;STL282780;AKOS002710300;2-allyl-propanedioic acid diethyl ester;AS-70112;SY027830;3-(3-ethylpent-2-enoxy)-3-oxo-propanoate;prop-2-enyl-propanedioic acid diethyl ester;A0231;CS-0011112;FT-0622049;EN300-85756;D88232;Diethyl allylmalonate, purum, >=95.0% (GC);A814606;J-013360;Z1258763580

Chemical Property of Diethyl allylmalonate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.101mmHg at 25°C
• Refractive Index: 1.4310
• Boiling Point: 222.499 °C at 760 mmHg
• PKA: 12.63±0.46(Predicted)
• Flash Point: 92.778 °C
• PSA: 52.60000
• Density: 1.021 g/cm³
• LogP: 1.30490
• Storage Temp.: Store below +30°C.
• Water Solubility.: Not miscible or difficult to mix with water.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 200.10485899
• Heavy Atom Count: 14
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

Diethyl allylmalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(CC=C)C(=O)OCC
• Uses: Diethyl allylmalonate is an important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals, agrochemicals and flavors and fragrances compounds.

Technology Process of Diethyl allylmalonate

There total 79 articles about Diethyl 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: 100.0%

allyl bromide (106-95-6) + diethyl malonate (105-53-3) → (2-propenyl)propanedioic acid diethyl ester (2049-80-1)

Guidance literature:

With tetrabutyl-ammonium chloride; potassium carbonate; In dichloromethane; water; at 80 ℃; for 45h;

Reference yield: 98.0%

Allyl acetate (591-87-7) + diethyl malonate (105-53-3) → (2-propenyl)propanedioic acid diethyl ester (2049-80-1)

Guidance literature:

With palladium diacetate; potassium fluoride on basic alumina; for 0.0833333h; microwave irradiation;

DOI:10.1016/S0040-4039(00)02027-X

Reference yield: 92.0%

allyl alcohol (107-18-6) + diethyl malonate (105-53-3) → (2-propenyl)propanedioic acid diethyl ester (2049-80-1)

Guidance literature:

With pyridine; magnesium sulfate; 1,2-(p-MeOC₆H₄)2cyclobuten[=P(2,4,6-tri-t-BuPh)]2PdOTf; at 50 ℃; for 12h;

DOI:10.1021/ja0274406

upstream raw materials:

allyl iodid

sodium diethylmalonate

ethanol

allylmalonic acid

Downstream raw materials:

5-allyl-2-amino-1H-pyrimidine-4,6-dione

5-allyl-pyrimidine-2,4,6-trione

2-phenyl-pent-4-enoic acid

diethyl 2-isobutyl-2-(prop-2-enyl)malonate

Refernces

• 1、 Vasil'ev, Andrei A.,Kuchurov, Ilya V.,Zlotin, Sergei G.. "Tsuji-Trost allylation of CH acids in supercritical carbon dioxide: Advantages and problems". . p. 84 - 85. Retrieved 2013.
• 2、 Blieck, Rémi,Azizi, Mohamed Salah,Mifleur, Alexis,Roger, Maxime,Persyn, Clément,Sauthier, Mathieu,Bonin, Hélène. "Nickel-Catalysed Bis-Allylation of Activated Nucleophiles with Allyl Alcohol". . p. 1194 - 1198. Retrieved 2016.
• 3、 Tsuji et al.. "". . p. 4387. Retrieved 1965.
• 4、 Ladoulis, Sandra J.,Nicholas, Kenneth M.. "Iron-catalyzed allylic alkylation". . p. C13-C16. Retrieved 1985.
• 5、 Lu, Xiyan,Lu, Ling. "REACTION OF ALLYLIC ARSENITES WITH LOW VALENT TRANSITION METAL COMPLEXES". . p. 285 - 290. Retrieved 1986.
• 6、 Masuyama, Yoshiro,Nakajima, Yukiko,Okabe, Jun. "Environmentally-benign palladium(II)-exchanged hydroxyapatite-catalyzed allylic alkylation of allyl methyl carbonate in water". . p. 107 - 112. Retrieved 2010.
• 7、 Pandey, Ganesh,Rao,Nageshwar Rao. "PhSeSiR3-catalyzed group transfer radical reactions". . p. 4309 - 4314. Retrieved 2000.
• 8、 Molander, Gary A.,Harris, Christina R.. "Sequenced reactions with samarium(II) iodide. Tandem intramolecular nucleophilic acyl substitution/intramolecular barbier cyclizations". . p. 3705 - 3716. Retrieved 1995.
• 9、 Veber,M. et al.. "". . p. 231 - 237. Retrieved 1979.
• 10、 Vasil'ev, Andrei A.,Zlotin, Sergei G.. "Palladium-catalyzed allylation of malonic acid derivatives in heterogeneous systems containing ionic liquids". . p. 23 - 25. Retrieved 2014.