Diethyl malonate

Diethyl malonate

Names
Preferred IUPAC name Diethyl propanedioate
Other names Diethyl malonate
Identifiers
CAS Number	105-53-3 Y
3D model (Jmol)	Interactive image
Abbreviations	DEM
Beilstein Reference	774687
ChEBI	CHEBI:391281 N
ChEMBL	ChEMBL177114 Y
ChemSpider	13863636 Y
ECHA InfoCard	100.003.006
EC Number	203-305-9
MeSH	Diethyl+malonate
PubChem	7761
RTECS number	OO0700000
UNII	53A58PA183 Y
InChI InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3 Y Key: IYXGSMUGOJNHAZ-UHFFFAOYSA-N Y InChI=1/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3 Key: IYXGSMUGOJNHAZ-UHFFFAOYAC
SMILES O=C(OCC)CC(=O)OCC
Properties
Chemical formula	C7H12O4
Molar mass	160.17 g/mol
Appearance	colourless liquid
Density	1.05 g/cm3, liquid
Melting point	−50 °C (−58 °F; 223 K)
Boiling point	199 °C (390 °F; 472 K)
Solubility in water	negligible
Acidity (pKa)	14
Magnetic susceptibility (χ)	-92.6·10−6 cm3/mol
Hazards
Main hazards	Harmful (X), Flammable (F)
Safety data sheet	Oxford University MSDS
Flash point	200 °C (392 °F; 473 K)
Related compounds
Related compounds	Dimethyl malonate Malonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B₁, and vitamin B₆.

Malonic acid is a rather simple dicarboxylic acid, with two the carboxyl groups close together. In forming diethyl malonate from malonic acid, the hydroxyl group (-OH) on both of the carboxyl groups is replaced by an ethoxy group (-OEt; -OCH₂CH₃). The methylene group (-CH₂-) in the middle of the malonic part of the diethyl malonate molecule is neighboured by two carbonyl groups (-C(=O)-).

The hydrogen atoms on the carbon adjacent to the carbonyl group in a molecule is significantly more acidic than hydrogen atoms on a carbon adjacent to alkyl groups (up to 30 orders of magnitude). (This is known as the α position with respect to the carbonyl.) The hydrogen atoms on a carbon adjacent to two carbonyl groups are even more acidic because on the – the carbonyl groups helps stabilize the carbanion resulting from the removal of a proton from the methylene group between them.

The extent of resonance stabilization of this compound's conjugate base is depicted by the three resonance forms below: