Question

Diethyl malonate anion is ... And reacts with alkyl halides to form diethyl alkyl malonate
(A) Hydrophilic
(B) Lipophilic
(C) Nucleophilic
(D) None​

Answer 1

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.

Diethyl malonate

Diethyl-malonate.png

Diethyl-malonate-3D-balls.png

Names

IUPAC name

Diethyl malonate[1]

Preferred IUPAC name

Diethyl propanedioate

Other names

Diethyl malonate

Identifiers

CAS Number

105-53-3 check

3D model (JSmol)

Interactive image

Abbreviations

DEM

Beilstein Reference

774687

ChEBI

CHEBI:391281 ☒

ChEMBL

ChEMBL177114 check

ChemSpider

13863636 check

ECHA InfoCard

100.003.006 Edit this at Wikidata

EC Number

203-305-9

MeSH

Diethyl+malonate

PubChem CID

7761

RTECS number

OO0700000

UNII

53A58PA183 check

CompTox Dashboard (EPA)

DTXSID7021863 Edit this at Wikidata

InChI

InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3 check

Key: IYXGSMUGOJNHAZ-UHFFFAOYSA-N check

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)