537349
Ethyl acetoacetate
ReagentPlus®, 99%
Synonym(s):
EAA, Ethyl 3-oxobutanoate, Acetoacetic ester
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About This Item
Linear Formula:
CH3COCH2COOC2H5
CAS Number:
Molecular Weight:
130.14
Beilstein:
385838
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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
Ethyl acetoacetate is a versatile reagent that can be used as a nucleophile in alkylation, conjugate addition and condensation reactions. 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.
- It also undergoes acylation at the α-carbon in the presence of MgCl2 and pyridine to give synthetically important intermediates.
- It can be used in Knoevenagel condensation with aliphatic, aromatic, and heteroaromatic aldehydes to produce α-alkylideneacetoacetates.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
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
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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