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537349

Sigma-Aldrich

Ethylacetoacetat

ReagentPlus®, 99%

Synonym(e):

EAA, Acetessigester

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About This Item

Lineare Formel:
CH3COCH2COOC2H5
CAS-Nummer:
141-97-9
Molekulargewicht:
130.14
Beilstein:
385838
EG-Nummer:
205-516-1
MDL-Nummer:
MFCD00009199
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24878213
NACRES:
NA.22

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Dampfdichte

4.48 (vs air)

Qualitätsniveau

200

Dampfdruck

1 mmHg ( 28.5 °C)

Produktlinie

ReagentPlus®

Assay

99%

Selbstzündungstemp.

580 °F

Expl.-Gr.

9.5 %

bp

181 °C (lit.)

mp (Schmelzpunkt)

−43 °C (lit.)

Löslichkeit

water: soluble 130 g/L at 20 °C

Dichte

1.029 g/mL at 20 °C (lit.)

Funktionelle Gruppe

ester
ketone

SMILES String

CCOC(=O)CC(C)=O

InChI

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

InChIKey

XYIBRDXRRQCHLP-UHFFFAOYSA-N

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Anwendung

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]

Rechtliche Hinweise

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

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 1

Flammpunkt (°F)

164.3 °F - closed cup

Flammpunkt (°C)

73.5 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCX1299
0000365285
0000325013
0000325013
MKCT5126

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Resorcinol ACS reagent, ≥99.0%

Sigma-Aldrich

398047

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ethyl 2-N-butylacetoacetate AldrichCPR

Sigma-Aldrich

CDS004004

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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)
Knoevenagel-kondensationen mit titantetrachlorid/base?II: Alkyliden-und arylidenacet-bzw.-nitroessigester bei 0?22?.
Lehnert W
Tetrahedron, 28(3), 663-666 (1972)
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)
Debasish Bandyopadhyay et al.
Molecules (Basel, Switzerland), 17(3), 2643-2662 (2012-03-07)
The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives. Bismuth nitrate pentahydrate under microwave irradiation is proven to act as a very efficient catalyst for
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Biginelli Reaction

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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  2. 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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