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537349

Sigma-Aldrich

Ethyl acetoacetate

ReagentPlus®, 99%

Sinônimo(s):

EAA, Ethyl 3-oxobutanoate, Acetoacetic ester

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R$ 647,00
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About This Item

Fórmula linear:
CH3COCH2COOC2H5
Número CAS:
141-97-9
Peso molecular:
130.14
Beilstein:
385838
Número CE:
205-516-1
Número MDL:
MFCD00009199
Código UNSPSC:
12352100
ID de substância PubChem:
24878213
NACRES:
NA.22

R$ 647,00

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densidade de vapor

4.48 (vs air)

Nível de qualidade

200

pressão de vapor

1 mmHg ( 28.5 °C)

linha de produto

ReagentPlus®

Ensaio

99%

temperatura de autoignição

580 °F

Lim. expl.

9.5 %

p.e.

181 °C (lit.)

pf

−43 °C (lit.)

solubilidade

water: soluble 130 g/L at 20 °C

densidade

1.029 g/mL at 20 °C (lit.)

grupo funcional

ester
ketone

cadeia de caracteres SMILES

CCOC(=O)CC(C)=O

InChI

1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

chave InChI

XYIBRDXRRQCHLP-UHFFFAOYSA-N

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Aplicação

Ethyl acetoacetate is a versatile reagent that can be used as a nucleophile in alkylation, conjugate addition and condensation reactions.[1] Some of its applications are:
  • Alkylation at the α-carbon of ethyl acetoacetate followed by hydrolysis and decarboxylation can afford a variety of methyl ketones.[2]
  • It also undergoes acylation at the α-carbon in the presence of MgCl2 and pyridine to give synthetically important intermediates.[3]
  • It can be used in Knoevenagel condensation with aliphatic, aromatic, and heteroaromatic aldehydes to produce α-alkylideneacetoacetates.[1][4]

Informações legais

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

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

164.3 °F - closed cup

Ponto de fulgor (°C)

73.5 °C - closed cup

Equipamento de proteção individual

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análise (COA)

Lot/Batch Number
MKCX1299
0000365285
0000325013
0000325013
MKCT5126

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Knoevenagel-kondensationen mit titantetrachlorid/base?II: Alkyliden-und arylidenacet-bzw.-nitroessigester bei 0?22?.
Lehnert W
Tetrahedron, 28(3), 663-666 (1972)
Synthetic Applications of Dealkoxycarbonylations of Malonate Esters, β-Keto Esters, α-Cyano Esters and Related Compounds in Dipolar Aprotic Media-Part II.
Krapcho A P
Synthesis, 1982(11), 893-914 (1982)
Ethyl Acetoacetate.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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)
Xiao-Ting Wang et al.
Journal of biotechnology, 163(3), 292-300 (2012-11-13)
The biocatalytic anti-Prelog stereoselective reduction of ethyl acetoacetate (EAA) to ethyl (R)-3-hydroxybutyrate {(R)-EHB} was successfully conducted in the aqueous system using immobilized Acetobacter sp. CCTCC M209061 cells. Among various microorganisms tested, Acetobacter sp. CCTCC M209061 gave the best performance and
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The Biginelli Reaction is an acid-catalyzed, three-component reaction between an aldehyde, b-ketoester, and urea that produces tetrahydropyrimidones, which have potential pharmaceutical applications.

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

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    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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    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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