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
537349
Ethyl acetoacetate
ReagentPlus®, 99%
Synonym(s):
EAA, Ethyl 3-oxobutanoate, Acetoacetic ester
About This Item
Recommended Products
vapor density
4.48 (vs air)
Quality Level
vapor pressure
1 mmHg ( 28.5 °C)
product line
ReagentPlus®
Assay
99%
autoignition temp.
580 °F
expl. lim.
9.5 %
bp
181 °C (lit.)
mp
−43 °C (lit.)
solubility
water: soluble 130 g/L at 20 °C
density
1.029 g/mL at 20 °C (lit.)
functional group
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
InChI key
XYIBRDXRRQCHLP-UHFFFAOYSA-N
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Application
- 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]
Legal Information
Storage Class Code
10 - Combustible liquids
WGK
WGK 1
Flash Point(F)
164.3 °F - closed cup
Flash Point(C)
73.5 °C - closed cup
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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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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.pdfHelpful?
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