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D97754

Sigma-Aldrich

Diethyl malonate

ReagentPlus®, 99%

Synonym(s):

Malonic acid diethyl ester

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About This Item

Linear Formula:
CH2(COOC2H5)2
CAS Number:
105-53-3
Molecular Weight:
160.17
Beilstein/REAXYS Number:
774687
EC Number:
203-305-9
MDL number:
MFCD00009195
UNSPSC Code:
12352100
PubChem Substance ID:
24894329
NACRES:
NA.22

vapor density

5.52 (vs air)

Quality Level

200

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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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
GHS07

signalword

Warning

hcodes

H319

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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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0477
STBL2460
STBK6705
STBJ8137
STBJ7048

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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)
Renhua Fan et al.
The Journal of organic chemistry, 72(15), 5905-5907 (2007-06-26)
A highly efficient, one-flask tandem Knoevenagel-Michael addition reaction of sulfonimines with diethyl malonate in the presence of a catalytic amount of base affords the corresponding arylidene dimalonates in good to excellent yields.
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Articles

Knoevenagel Condensation Reaction

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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