Diethyl allylmalonate

Diethyl allylmalonate Basic information
Product Name:Diethyl allylmalonate
Synonyms:2-Propenylmalonic acid diethyl ester;3-Butene-1,1-dicarboxylic acid diethyl ester;Allylmalonic acid diethyl;Diethyl allylmalonate,97%;Diethyl allyl;Diethyl allylMalonate, 97% 500GR;2-propenyl-propanedioicacidiethylester;Diethyl 2-(2-propenyl)-1,3-propanedioate
CAS:2049-80-1
MF:C10H16O4
MW:200.23
EINECS:218-072-9
Product Categories:Pharmaceutical Intermediates;Aromatic Esters;TheMalonateRamificationProducts
Mol File:2049-80-1.mol
Diethyl allylmalonate Structure
Diethyl allylmalonate Chemical Properties
Boiling point 222-223 °C(lit.)
density 1.015 g/mL at 25 °C(lit.)
refractive index n20/D 1.431(lit.)
Fp 160 °F
storage temp. Store below +30°C.
pka12.63±0.46(Predicted)
form Liquid
color Clear colorless to slightly yellow
Water Solubility Not miscible or difficult to mix with water.
BRN 1709466
LogP1.990 (est)
CAS DataBase Reference2049-80-1(CAS DataBase Reference)
NIST Chemistry ReferencePropanedioic acid, 2-propenyl-, diethyl ester(2049-80-1)
EPA Substance Registry SystemPropanedioic acid, 2-propenyl-, diethyl ester (2049-80-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
RIDADR NA 1993 / PGIII
WGK Germany 3
TSCA Yes
HS Code 29171990
MSDS Information
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Diethyl allylmalonate Usage And Synthesis
Chemical Propertiesclear colorless to slightly yellow liquid
UsesDiethyl 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.
PreparationDiethyl allyl malonate is obtained by reacting diethyl malonate with allyl bromide.
Under nitrogen atmosphere, to a 500 mL three-neck round bottom flask was added diethyl malonate (20 g), anhydrous potassium carbonate (43 g) and anhydrous CH3CN (200 mL). The reaction mixture was stirred at room temperature for 10 minutes, then allyl bromide (23 g) was slowly added to the reaction mixture at room temperature. The reaction mixture was heated to 80°C for 24 hours. The reaction mixture was cooled to room temperature and filtered through a bed of celite. The celite bed was washed with acetonitrile (100 mL) and the combined filtrates were concentrated to give diethyl allylmalonate (24 g) as a colorless liquid.
Synthesis Reference(s)Chemistry Letters, 17, p. 291, 1988
The Journal of Organic Chemistry, 28, p. 504, 1963 DOI: 10.1021/jo01037a058
Diethyl allylmalonate Preparation Products And Raw materials
Raw materialsDIETHYL DIALLYLMALONATE-->Diethyl malonate
Preparation ProductsEthyl 2-methyl-4-pentenoate-->5-ACETALDEHYDEYL-4,6-DICHLOROPYRIMIDINE
Diethyl dipropylmalonate Diethyl benzylmalonate ALLYL-1-METHYLBUTYLDIETHYL MALONATE Diethyl isopropylmalonate Diethyl phenylmalonate Diethyl bis(hydroxymethyl)malonate Diethyl phthalate 2-AMINODIETHYLMALONATE Tris(trimethylsilyl)phosphate Diethyl butylmalonate DIETHYL DIETHYLMALONATE Diethyl methylmalonate Diethyl ether Celiprolol Methyl acrylate Diethyl allylmalonate Dimethyl succinate 2-VINYLCYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER

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