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688983

Sigma-Aldrich

Ethyl acetoacetate

Arxada quality, ≥99.0% (GC)

Synonym(s):

Acetoacetic ester

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About This Item

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:
329761207
NACRES:
NA.22

vapor density

4.48 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 28.5 °C)

assay

≥99.0% (GC)

form

liquid

autoignition temp.

580 °F

quality

Arxada quality

expl. lim.

9.5 %

manufacturer/tradename

Arxada AG

impurities

≤0.05% water
≤0.10% acid (as acetic acid)

color

APHA: ≤15

bp

180 °C
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

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Application

Ethyl acetoacetate can undergo:
  • Transesterification with primary and secondary alcohols in the presence of boric acid.
  • Microbial reduction to form (S)-ethyl 3-hydroxybutyrate.
  • C-acylation by acid chlorides in the presence of magnesium chloride and pyridine.
  • Asymmetric biphasic catalytic hydrogenation in the presence of a water-soluble ruthenium-BINAP complex.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hydrogenation of ethyl acetoacetate catalyzed by hydrosoluble BINAP derivatives
Lamouille T, et al.
Tetrahedron Letters, 42(4), 663-664 (2001)
Production of (+)-(S)-Ethyl 3-Hydroxybutyrate and (−)-(R)-Ethyl 3-Hydroxybutyrate by Microbial Reduction of Ethyl Acetoacetate
Wipf B, et al.
Helvetica Chimica Acta, 66(2), 485-488 (1983)
Enantioselective catalytic asymmetric hydrogenation of ethyl acetoacetate in room temperature ionic liquids
Berthod M, et al.
Tetrahedron Asymmetry, 15(14), 2219-2221 (2004)
Boric acid: an efficient and environmentally benign catalyst for transesterification of ethyl acetoacetate
Kondaiah GCM, et al.
Tetrahedron Letters, 49(1), 106-109 (2008)
Procedures for the acylation of diethyl malonate and ethyl acetoacetate with acid chlorides using tertiary amine bases and magnesium chloride.
Rathke MW and Cowan PJ.
The Journal of Organic Chemistry, 50(15), 2622-2624 (1985)
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