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D97754

Sigma-Aldrich

Diethyl malonate

ReagentPlus®, 99%

Sinônimo(s):

Malonic acid diethyl ester

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25 G
R$ 277,00
500 G
R$ 349,00
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R$ 688,00
2.5 KG
R$ 1.146,00

R$ 277,00

Disponível para enviar em17 de abril de 2025Detalhes

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25 G
R$ 277,00
500 G
R$ 349,00
1 KG
R$ 688,00
2.5 KG
R$ 1.146,00

About This Item

Fórmula linear:
CH2(COOC2H5)2
Número CAS:
105-53-3
Peso molecular:
160.17
Beilstein:
774687
Número CE:
203-305-9
Número MDL:
MFCD00009195
Código UNSPSC:
12352100
ID de substância PubChem:
24894329
NACRES:
NA.22

R$ 277,00

Disponível para enviar em17 de abril de 2025Detalhes

Solicite uma grande encomenda

densidade de vapor

5.52 (vs air)

pressão de vapor

1 mmHg ( 40 °C)

linha de produto

ReagentPlus®

Ensaio

99%

Formulário

liquid

índice de refração

n20/D 1.413 (lit.)

p.e.

199 °C (lit.)

pf

−51-−50 °C (lit.)

densidade

1.055 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

CCOC(=O)CC(=O)OCC

InChI

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

chave InChI

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

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Descrição geral

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]

Aplicação

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]

Embalagem

Packaged in glass bottles

Informações legais

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

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H319

Classificações de perigo

Eye Irrit. 2

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

199.4 °F - closed cup

Ponto de fulgor (°C)

93 °C - closed cup

Equipamento de proteção individual

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

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Certificados de análise (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)
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)
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Artigos

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. 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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