Ethyl acetoacetate

Name: Ethyl acetoacetate
Brand: ALDRICH

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

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

329761207

EC Number:

205-516-1

Beilstein/REAXYS Number:

385838

MDL number:

MFCD00009199

Product Name

Ethyl acetoacetate, Arxada quality, ≥99.0% (GC)

InChI key

XYIBRDXRRQCHLP-UHFFFAOYSA-N

InChI

1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

SMILES string

CCOC(=O)CC(C)=O

vapor density

4.48 (vs air)

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.)

Quality Level

200

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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

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

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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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