8.09622

Ethyl acetoacetate

for synthesis

• Synonym(s): Ethyl acetoacetate, EAA, Acetoacetic acid ethyl ester
• Empirical Formula (Hill Notation): C₆H₁₀O₃
• CAS Number: 141-97-9
• Molecular Weight: 130.14
• MDL number: MFCD00009199
• UNSPSC Code: 12352108
• EC Index Number: 205-516-1
• NACRES: NA.22

Properties

• vapor pressure: 0.26 hPa ( 20 °C)
• Quality Level: 200
• Assay: ≥98.0% (GC)
• form: liquid
• autoignition temp.: 350 °C
• potency: 3980 mg/kg LD₅₀, oral (Rat); >5000 mg/kg LD₅₀, skin (Rabbit)
• expl. lim.: 1.0-54 % (v/v)
• pH: 4.0 (20 °C, 110 g/L in H₂O)
• mp: -53.3 °C
• transition temp: flash point 73.5 °C
• solubility: 130.3 g/L
• density: 1.03 g/cm³ at 20 °C
• storage temp.: 2-30°C
• SMILES string: O(CC)C(=O)CC(=O)C
• 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 can be used as a reactant to synthesize:

• 7-hydroxycoumarin derivatives via Pechmann condensation reaction with 1,3-dihydroxybenzene in the presence of acid catalysts.
• 2,6-disubstituted piperidine alkaloid, (−)-pinidinone via stereoselective α-aminoallylation followed by Grubbs′ olefin cross-metathesis reaction.
• Michael addition products via Michael addition reaction with chalcones and azachalcones in the presence of a base catalyst.
• α, β-unsaturated carbonyl compounds via Knoevenagel condensation reaction with glyceraldehyde acetonide in the presence of a base catalyst.

It can be also utilized as a reactant in the transesterification and asymmetric hydrogenation reactions to produce valuable products.

Analysis Note

Assay (GC, area%): ≥ 98.0 % (a/a)
Density (d 20 °C/ 4 °C): 1.028 - 1.030
Identity (IR): passes test

Safety 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