Diethyl malonate

The CAS registry number of Diethyl malonate is 105-53-3. The IUPAC name is diethyl propanedioate. In addition, the molecular formula is C₇H₁₂O₄ and the molecular weight is 160.17. It is also called propanedioic acid, diethyl ester. What's more, it is the diethyl ester of malonic acid. And it is a colourless liquid with an apple-like odour. Besides, it can be used in perfumes. It is also used to synthesize other compounds such as barbiturates and artificial flavourings.

Physical properties about this chemical are: (1)ACD/LogP: 0.70; (2)ACD/LogD (pH 5.5): 0.7; (3)ACD/LogD (pH 7.4): 0.7; (4)ACD/BCF (pH 5.5): 2.02; (5)ACD/BCF (pH 7.4): 2.02; (6)ACD/KOC (pH 5.5): 57.48; (7)ACD/KOC (pH 7.4): 57.48; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 6; (10)Polar Surface Area: 52.6 Å²; (11)Index of Refraction: 1.417; (12)Molar Refractivity: 38.02 cm³; (13)Molar Volume: 151 cm³; (14)Polarizability: 15.07 ×10^-24cm³; (15)Surface Tension: 32.3 dyne/cm; (16)Density: 1.06 g/cm³; (17)Flash Point: 100 °C; (18)Enthalpy of Vaporization: 43.55 kJ/mol; (19)Boiling Point: 199.3 °C at 760 mmHg; (20)Vapour Pressure: 0.344 mmHg at 25°C.

Preparation of Diethyl malonate: it can be prepared by reacting the sodium salt of chloroacetic acid with sodium cyanide, followed by base hydrolysis of the resultant nitrile to give the sodium salt malonic acid.

Uses of Diethyl malonate: One of the principle uses of this compound is in the malonic ester synthesis. And it can react with 1,2-dichloro-ethane to get cyclopropane-1,1-dicarboxylic acid diethyl ester. This reaction will need reagents K₂CO₃ and H₂O, catalyst (n-Bu)₄N(1+)Br(1-) and solvent benzene. The reaction time is 12 hours at reaction temperature of 80 °C. The yield is about 85%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. During using it, you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)CC(=O)OCC
(2)InChI: InChI=1/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3
(3)InChIKey: IYXGSMUGOJNHAZ-UHFFFAOYAC

The toxicity data is as follows: