537349

Ethyl acetoacetate

ReagentPlus^®, 99%

• Synonym(s): EAA, Ethyl 3-oxobutanoate, Acetoacetic ester
• Linear Formula: CH₃COCH₂COOC₂H₅
• CAS Number: 141-97-9
• Molecular Weight: 130.14
• Beilstein/REAXYS Number: 385838
• EC Number: 205-516-1
• MDL number: MFCD00009199
• UNSPSC Code: 12352100
• PubChem Substance ID: 24878213
• NACRES: NA.22

Properties

• vapor density: 4.48 (vs air)
• 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.)
• 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

Description

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

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 1
• flash_point_f: 164.3 °F - closed cup
• flash_point_c: 73.5 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter