8.09622

Ethyl acetoacetate

for synthesis

• Synonyme(s) : Ethyl acetoacetate, EAA, Acetoacetic acid ethyl ester
• Formule empirique (notation de Hill): C₆H₁₀O₃
• Numéro CAS: 141-97-9
• Poids moléculaire : 130.14
• Numéro MDL: MFCD00009199
• Code UNSPSC : 12352108
• Numéro de classement CE : 205-516-1
• Nomenclature NACRES : NA.22

Propriétés

• Pression de vapeur: 0.26 hPa ( 20 °C)
• Niveau de qualité: 200
• Pureté: ≥98.0% (GC)
• Forme: liquid
• Température d'inflammation spontanée: 350 °C
• Puissance: 3980 mg/kg LD₅₀, oral (Rat); >5000 mg/kg LD₅₀, skin (Rabbit)
• Limite d'explosivité: 1.0-54 % (v/v)
• pH: 4.0 (20 °C, 110 g/L in H₂O)
• Pf: -53.3 °C
• Température de transition: flash point 73.5 °C
• Solubilité: 130.3 g/L
• Densité: 1.03 g/cm³ at 20 °C
• Température de stockage: 2-30°C
• InChI: 1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
• Clé InChI: 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.

Remarque sur l'analyse

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

Informations sur la sécurité

• Code de la classe de stockage: 10 - Combustible liquids
• Classe de danger pour l'eau (WGK): WGK 1
• Point d'éclair (°F): 164.3 °F - closed cup
• Point d'éclair (°C): 73.5 °C - closed cup