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D97754

Sigma-Aldrich

Diethylmalonat

ReagentPlus®, 99%

Synonym(e):

Diethyl-malonat

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€ 32,90
500 G
€ 41,40
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€ 81,70
2.5 KG
€ 136,00

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25 G
€ 32,90
500 G
€ 41,40
1 KG
€ 81,70
2.5 KG
€ 136,00

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

€ 32,90

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Dampfdichte

5.52 (vs air)

Qualitätsniveau

200

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.[1] Acylation of diethyl malonate using magnesium chloride and triethylamine is reported.[2] K2CO3-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.[3]

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.[4] It may be used in the synthesis of diethyl benzylidenemalonate by base catalyzed Knoevenagel condensation with benzaldehyde.[5] It may be used in the synthesis of α-aryl malonates.[6]

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)

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
SDBB0477
STBL2460
STBK6705
STBJ8137
STBJ7048

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Dimethylmalonat purum, ≥96.0% (GC)

Sigma-Aldrich

63380

Dimethylmalonat

Natriumethoxid 95%

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)
Procedures for the acylation of diethyl malonate and ethyl acetoacetate with acid chlorides using tertiary amine bases and magnesium chloride.
Rathke MW and Cowan PJ.
The Journal of Organic Chemistry, 50(15), 2622-2624 (1985)
Alle zugehörigen Dokumente anzeigen

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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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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