00410

Ethyl acetoacetate

puriss. p.a., ≥99.0% (GC)

• Synonym(s): 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
• eCl@ss: 39022303
• PubChem Substance ID: 329747065
• NACRES: NA.22

Properties

• vapor density: 4.48 (vs air)
• Quality Level: 200
• vapor pressure: 1 mmHg ( 28.5 °C)
• grade: puriss. p.a.
• assay: ≥99.0% (GC)
• autoignition temp.: 580 °F
• expl. lim.: 9.5 %
• impurities: ≤0.5% water
• refractive index: n20/D 1.419
• 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.)
• cation traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤0.5 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.5 mg/kg
• 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

Description

Application

Ethyl acetoacetate can be used as a reactant in the synthesis of:

• Knoevenagel condensation products by reacting with α-alkylideneacetoacetate and aliphatic, aromatic, heteroaromatic aldehydes.
• Michael adducts, via Michael addition reaction with chalcones and azachalcones in the presence of a base catalyst.
• Substituted nicotinic acid derivatives by treating with α, β-unsaturated oximes via Michael addition followed by ring closure reaction.

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

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