Diethyl malonate

Diethyl malonate
Names
	IUPAC name Diethyl malonate
	Preferred IUPAC name Diethyl propanedioate
	Other names Diethyl malonate
Identifiers
CAS Number	105-53-3 ;
3D model (JSmol)	Interactive image;
Abbreviations	DEM
Beilstein Reference	774687
ChEBI	CHEBI:391281 ;
ChEMBL	ChEMBL177114 ;
ChemSpider	13863636 ;
ECHA InfoCard	100.003.006
EC Number	203-305-9;
MeSH	Diethyl+malonate
PubChem CID	7761;
RTECS number	OO0700000;
UNII	53A58PA183 ;
CompTox Dashboard (EPA)	DTXSID7021863 ;
	InChI InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3 Key: IYXGSMUGOJNHAZ-UHFFFAOYSA-N ; 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; 16.37 (DMSO)
Magnetic susceptibility (χ)	-92.6·10−6 cm3/mol
Structure
Dipole moment	2.54 D (liquid)
Thermochemistry
Heat capacity (C)	285.0 J·mol−1·K−1
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Harmful (X), Flammable (F)
Flash point	93 °C (199 °F; 366 K)
Safety data sheet (SDS)	Oxford University MSDS
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). verify (what is ?) 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 recognised as a valid, expert-verified name for what would systematically be called 'propanedioic acid' according to ChemSpider.
^ Olmstead, William N.; Bordwell, Frederick G. (1980). "Ion-pair association constants in dimethyl sulfoxide". The Journal of Organic Chemistry. 45 (16): 3299–3305. doi:10.1021/jo01304a033.
^ ^a ^b ^c CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)

Names


IUPAC name Diethyl malonate^[1]
Preferred IUPAC name Diethyl propanedioate
Other names Diethyl malonate
Identifiers
CAS Number	105-53-3^Y
3D model (JSmol)	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 CID	7761
RTECS number	OO0700000
UNII	53A58PA183^Y
CompTox Dashboard (EPA)	DTXSID7021863
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 (pK_a)	14 16.37 (DMSO)^[2]
Magnetic susceptibility (χ)	-92.6·10⁻⁶ cm³/mol
Structure
Dipole moment	2.54 D (liquid)^[3]
Thermochemistry
Heat capacity (C)	285.0 J·mol⁻¹·K⁻¹^[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful (X), Flammable (F)
Flash point	93 °C (199 °F; 366 K)^[3]
Safety data sheet (SDS)	Oxford University MSDS
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 verify (what is ^YN ?) Infobox references