8.09622
Ethyl acetoacetate
for synthesis
别名:
Ethyl acetoacetate, EAA, Acetoacetic acid ethyl ester
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关于此项目
经验公式（希尔记法）:
C6H10O3
化学文摘社编号:
分子量:
130.14
UNSPSC Code:
12352108
EC Index Number:
205-516-1
NACRES:
NA.22
MDL number:
产品名称
Ethyl acetoacetate, for synthesis
SMILES string
O(CC)C(=O)CC(=O)C
InChI
1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChI key
XYIBRDXRRQCHLP-UHFFFAOYSA-N
vapor pressure
0.26 hPa ( 20 °C)
assay
≥98.0% (GC)
form
liquid
autoignition temp.
350 °C
potency
3980 mg/kg LD50, oral (Rat)
>5000 mg/kg LD50, skin (Rabbit)
expl. lim.
1.0-54 % (v/v)
pH
4.0 (20 °C, 110 g/L in H2O)
mp
-53.3 °C
transition temp
flash point 73.5 °C
solubility
130.3 g/L
density
1.03 g/cm3 at 20 °C
storage temp.
2-30°C
Quality Level
Analysis Note
Assay (GC, area%): ≥ 98.0 % (a/a)
Density (d 20 °C/ 4 °C): 1.028 - 1.030
Identity (IR): passes test
Density (d 20 °C/ 4 °C): 1.028 - 1.030
Identity (IR): passes test
Application
Ethyl acetoacetate can be used as a reactant to synthesize:
It can be also utilized as a reactant in the transesterification and asymmetric hydrogenation reactions to produce valuable products.
- 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.
存储类别
10 - Combustible liquids
wgk
WGK 1
flash_point_f
164.3 °F - closed cup
flash_point_c
73.5 °C - closed cup
An Expeditious Stereoselective Synthesis of (-)-Pinidinone from Ethyl Acetoacetate
Damodar K and Jun Jong-Gab
Bulletin of the Korean Chemical Society,, 37(4), 571-575 (2016)
Condensation of glyceraldehyde acetonide with ethyl acetoacetate over Mg, Al-mixed oxides derived from hydrotalcites
Veloso Claudia O, et al.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 107(1-2), 23-30 (2008)
Synthesis of 7-hydroxycoumarins catalysed by solid acid catalysts
Hoefnagel AJ, et al.
Journal of the Chemical Society. Chemical Communications, (2), 225-226 (1995)
Mechanochemical Michael reactions of chalcones and azachalcones with ethyl acetoacetate catalyzed by K2CO3 under solvent-free conditions
Zhang Ze, et al.
Chemistry Letters (Jpn), 33(2), 168-169 (2004)
Enantioselective catalytic asymmetric hydrogenation of ethyl acetoacetate in room temperature ionic liquids
Berthod M, et al.
Tetrahedron Asymmetry, 15(14), 2219-2221 (2004)
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