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D97754

Sigma-Aldrich

Diethyl malonate

ReagentPlus®, 99%

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Synonym(s):
Malonic acid diethyl ester
Linear Formula:
CH2(COOC2H5)2
CAS Number:
Molecular Weight:
160.17
Beilstein/REAXYS Number:
774687
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

5.52 (vs air)

Quality Level

vapor pressure

1 mmHg ( 40 °C)

product line

ReagentPlus®

assay

99%

form

liquid

refractive index

n20/D 1.413 (lit.)

bp

199 °C (lit.)

mp

−51-−50 °C (lit.)

density

1.055 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CC(=O)OCC

InChI

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

InChI key

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

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1 of 4

This Item
W2375078.008988.00899
Diethyl malonate ReagentPlus®, 99%

D97754

Diethyl malonate

Diethyl malonate ≥98%, FG

W237507

Diethyl malonate

Diethyl malonate for synthesis

8.00898

Diethyl malonate

Dimethyl malonate for synthesis

8.00899

Dimethyl malonate

Quality Level

200

Quality Level

400

Quality Level

200

Quality Level

200

mp

−51-−50 °C (lit.)

mp

−51-−50 °C (lit.)

mp

-50 °C

mp

-61.9 °C

density

1.055 g/mL at 25 °C (lit.)

density

1.055 g/mL at 25 °C (lit.)

density

1.055 g/cm3 at 20 °C

density

1.15 g/cm3 at 20 °C

bp

199 °C (lit.)

bp

199 °C (lit.)

bp

199 °C/1013 hPa

bp

181-183 °C/1013 hPa

form

liquid

form

-

form

liquid

form

liquid

General description

Diethyl malonate is diethyl ester of malonic acid. It is widely used as a versatile building block for introducing the malonate functional group into molecules. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K2CO3-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.

Application

Diethyl malonate was used to investigate Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites. It may be used in the synthesis of diethyl benzylidenemalonate by base catalyzed Knoevenagel condensation with benzaldehyde. It may be used in the synthesis of α-aryl malonates.

Packaging

Packaged in glass bottles

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

199.4 °F - closed cup

flash_point_c

93 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


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Shengming Ma et al.
The Journal of organic chemistry, 68(23), 8996-9002 (2003-11-08)
The K2CO3 (10 mol %)-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones leading to polyfunctionalized beta,gamma-unsaturated enones 3 or 4 was studied. With 3-unsubstituted 1-substituted-1,2-allenyl ketones, the highly selective formation of beta,gamma-unsaturated enones 4 was observed; with
Solvent-free organocatalytic Michael addition of diethyl malonate to nitroalkenes: the practical synthesis of Pregabalin and ?-nitrobutyric acid derivatives
J Liu, et al.
Tetrahedron, 67, 636-640 (2011)
Edward J Hennessy et al.
Organic letters, 4(2), 269-272 (2002-02-14)
[reaction: see text] A general method for the synthesis of alpha-aryl malonates is described. The coupling of an aryl iodide and diethyl malonate in the presence of Cs(2)CO(3) and catalytic amounts of copper(I) iodide and 2-phenylphenol affords the alpha-aryl malonate
Integration of heterogeneous catalysts into complex synthetic routes: sequential vs. one-pot reactions in a (Knoevenagel+ Mukaiyama-Michael+ hydrogenation+ transesterification) sequence.
Fraile JM, et al.
Catalysis Science & Technology, 3(2), 436-443 (2013)
Faqiang Leng et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(54), 13379-13386 (2017-05-26)
The C

Articles

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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