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D97754

Sigma-Aldrich

Diethylmalonat

ReagentPlus®, 99%

Synonym(e):

Diethyl-malonat

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About This Item

Lineare Formel:
CH2(COOC2H5)2
CAS-Nummer:
105-53-3
Molekulargewicht:
160.17
Beilstein:
774687
EG-Nummer:
203-305-9
MDL-Nummer:
MFCD00009195
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24894329
NACRES:
NA.22

Dampfdichte

5.52 (vs air)

Dampfdruck

1 mmHg ( 40 °C)

Produktlinie

ReagentPlus®

Assay

99%

Form

liquid

Brechungsindex

n20/D 1.413 (lit.)

bp

199 °C (lit.)

mp (Schmelzpunkt)

−51-−50 °C (lit.)

Dichte

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

InChIKey

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

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Verwandte Kategorien

Allgemeine Beschreibung

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.

Anwendung

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.

Verpackung

Packaged in glass bottles

Rechtliche Hinweise

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H319

Gefahreneinstufungen

Eye Irrit. 2

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 1

Flammpunkt (°F)

199.4 °F - closed cup

Flammpunkt (°C)

93 °C - closed cup

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Sigma-Aldrich

63380

Dimethylmalonat

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Sigma-Aldrich

156248

Natriumethoxid

Dimethylmalonat for synthesis

Sigma-Aldrich

8.00899

Dimethylmalonat

Diisopropylmalonat ReagentPlus®, 99%

Sigma-Aldrich

411485

Diisopropylmalonat

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)
Lian Jin Liu et al.
Nucleosides, nucleotides & nucleic acids, 30(10), 784-797 (2011-10-05)
Novel 5'-norcarbocyclic adenosine phosphonic acid analogues with 6'-electropositive moiety such as spirocyclopropane were designed and synthesized from the commercially available diethylmalonate 5. Regioselective Mitsunobu reaction proceeded in the presence of an allylic functional group at a low reaction temperature in
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Artikel

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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