DIETHYL DIALLYLMALONATE Chemical Properties

Boiling point:

128-130 °C/12 mmHg (lit.)

Density 

0.994 g/mL at 25 °C (lit.)

vapor pressure 

4.266Pa at 25℃

refractive index 

n20/D 1.446(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, DMSO, Methanol

form 

Oil

color 

Clear Colourless

Water Solubility 

Sparingly Soluble in water. (0.72 g/L) (25°C)

BRN 

1790529

InChI

1S/C13H20O4/c1-5-9-13(10-6-2,11(14)16-7-3)12(15)17-8-4/h5-6H,1-2,7-10H2,3-4H3

InChIKey

LYUUVYQGUMRKOV-UHFFFAOYSA-N

SMILES

CCOC(=O)C(CC=C)(CC=C)C(=O)OCC

LogP

3.46

CAS DataBase Reference

3195-24-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2917198090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

DIETHYL DIALLYLMALONATE Usage And Synthesis

Uses

Diethyl diallylmalonate is the starting material for enantioselective synthesis of carbocyclic nucleoside analogues. It is also used as Low catalyst loading in ring-closing metathesis reaction. Cationic nickel (with monodentate phosphoramidites and Wilke?s azaphospholene as ligands) catalyzed cycloisomerisation of diethyl diallylmalonate has been reported.

Definition

ChEBI: Diethyl diallylmalonate is a fatty acid ester.

General Description

Low catalyst loading in ring-closing metathesis reaction of diethyl diallylmalonate has been reported. Cationic nickel (with monodentate phosphoramidites and Wilke′s azaphospholene as ligands) catalyzed cycloisomerisation of diethyl diallylmalonate has been reported.

Synthesis

To a mixture of diethyl malonate (10 g, 62.5 mmol) and allyl bromide (14.25 g, 187.5 mmol), a concentrated solution of sodium ethanolate (70 mL ethanol solution of 8.6 g sodium) was slowly added between 5-10??C with continuous stirring. After the addition of sodium ethoxide, the reaction mixture was stirred at the same temperature for another 1 h. The cold water bath was then removed and the mixture was stirred at room temperature overnight. The excess solvent was removed and the residue was added to water and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and evaporated to give a light yellow liquid. The crude substance was purified by vacuum distillation to give a colorless liquid.

DIETHYL DIALLYLMALONATE(3195-24-2)Related Product Information

• PROPYLMALONIC ACID
• 2-ALLYL-4-PENTENOIC ACID
• Diethyl dipropylmalonate
• 2-Propylvaleric acid methyl ester
• 2-Acetyl-2-propylvaleric acid methyl ester
• 2,2-Dipropylmalonic acid
• ETHYL N-PROPYL ETHER
• 1-Chloropropane
• Malonic acid
• Allyl chloride
• Valproic acid Impurity(244Da)
• Pentanamide
• 2-(1-methylethyl)-2-propyl-Propanedioic acid
• Pentanoic acid, 2-cyano-, methyl ester
• Valeronitrile
• Valeric acid
• Pentanamide, 2-ethyl-
• 4-Hydroxy Valproic Acid Sodium Salt(Mixture of diastereomers)