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D97754

Sigma-Aldrich

Diethyl malonate

ReagentPlus®, 99%

Sinónimos:

Malonic acid diethyl ester

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25 G
21,60 €
500 G
51,40 €
1 KG
102,00 €
2.5 KG
161,00 €

21,60 €

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25 G
21,60 €
500 G
51,40 €
1 KG
102,00 €
2.5 KG
161,00 €

About This Item

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

21,60 €

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densidad de vapor

5.52 (vs air)

presión de vapor

1 mmHg ( 40 °C)

Línea del producto

ReagentPlus®

Ensayo

99%

Formulario

liquid

índice de refracción

n20/D 1.413 (lit.)

bp

199 °C (lit.)

mp

−51-−50 °C (lit.)

densidad

1.055 g/mL at 25 °C (lit.)

cadena SMILES

CCOC(=O)CC(=O)OCC

InChI

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

Clave InChI

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

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Descripción general

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]

Aplicación

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]

Envase

Packaged in glass bottles

Información legal

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

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H319

Clasificaciones de peligro

Eye Irrit. 2

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

199.4 °F - closed cup

Punto de inflamabilidad (°C)

93 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (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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Artículos

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 respuesta

    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 respuesta

    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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