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00410 Sigma-Aldrich

Ethyl acetoacetate

puriss. p.a., ≥99.0% (GC)

Synonym: Acetoacetic ester

  • CAS Number 141-97-9

  • Linear Formula CH3COCH2COOC2H5

  • Molecular Weight 130.14

  •  Beilstein/REAXYS Number 385838

  •  EC Number 205-516-1

  •  MDL number MFCD00009199

  •  eCl@ss 39022303

  •  PubChem Substance ID 329747065

  •  NACRES NA.22

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Properties

Related Categories Analytical Reagents, Analytical Reagents for General Use, Analytical/Chromatography, Arbidol, Building Blocks,
Quality Level   200
vapor density   4.48 (vs air)
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
storage temp.   room temp
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 & Documentation

Safety Information

WGK Germany 
WGK 1
RTECS 
AK5250000
Flash Point(F) 
164.3 °F - closed cup
Flash Point(C) 
73.5 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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