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W241504

Sigma-Aldrich

Ethyl acetoacetate

≥99%, FCC, FG

Synonym(s):

Acetoacetic ester

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About This Item

Linear Formula:
CH3COCH2COOC2H5
CAS Number:
141-97-9
Molecular Weight:
130.14
FEMA Number:
2415
Beilstein/REAXYS Number:
385838
EC Number:
205-516-1
Council of Europe no.:
240
MDL number:
MFCD00009199
UNSPSC Code:
12164502
PubChem Substance ID:
24901055
Flavis number:
9.402
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Kosher

agency

meets purity specifications of JECFA

reg. compliance

EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 117
FDA 21 CFR 172.515

vapor density

4.48 (vs air)

vapor pressure

1 mmHg ( 28.5 °C)

assay

≥99%

autoignition temp.

580 °F

expl. lim.

9.5 %

refractive index

n20/D 1.418-1.421

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.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

apple; fatty; green; fruity

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


  • Fabrication of a novel magnetic nanostructure based on cellulose-gellan gum hydrogel, embedded with MgAl LDH as an efficient catalyst for the synthesis of polyhydroquinoline derivatives.: This study explores the use of ethyl acetoacetate in the synthesis of polyhydroquinoline derivatives, showcasing its application in developing efficient catalytic systems for organic reactions (Hjazi A, 2024).

  • Evaluation of diethyl 4-(5-bromo-1H-indol-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate: synthesis, anti-corrosion potential, and biomedical applications.: This research investigates the biomedical applications and anti-corrosion properties of compounds synthesized using ethyl acetoacetate, emphasizing its versatility in chemical synthesis and material science (Ahamed FMM et al., 2024).

  • Fe(3)O(4) nanoparticles impregnated eggshell as an efficient biocatalyst for eco-friendly synthesis of 2-amino thiophene derivatives.: The study highlights the use of ethyl acetoacetate in green chemistry, particularly in the eco-friendly synthesis of thiophene derivatives using biocatalysts (Zargari M et al., 2024).

  • Pyrano[2,3-c]pyrazole fused spirooxindole-linked 1,2,3-triazoles as antioxidant agents: Exploring their utility in the development of antidiabetic drugs via inhibition of α-amylase and DPP4 activity.: This paper discusses the synthesis of novel compounds with antidiabetic properties using ethyl acetoacetate, demonstrating its potential in drug development (Chahal S et al., 2024).

  • Access to Functionalized Cyclohex-2-enones from a Multicomponent Cascade Reaction of Readily Available Alkynes, Ketones, and Ethyl Acetoacetate.: The research details a multicomponent cascade reaction involving ethyl acetoacetate, highlighting its utility in the efficient synthesis of functionalized cyclohexenones (Jiang D et al., 2024).

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)

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Debasish Bandyopadhyay et al.
Molecules (Basel, Switzerland), 17(3), 2643-2662 (2012-03-07)
The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives. Bismuth nitrate pentahydrate under microwave irradiation is proven to act as a very efficient catalyst for
Arne T Dickschat et al.
Chemical communications (Cambridge, England), 49(22), 2195-2197 (2013-02-09)
Bifunctional mesoporous silica nanoparticles (MSNs) bearing Pd-complexes and additional basic sites were prepared and tested as cooperative active catalysts in the Tsuji-Trost allylation of ethyl acetoacetate. Functionalization of the MSNs was realized by postmodification using click-chemistry. The selectivity of mono
Gui-Rong Qu et al.
Organic letters, 11(8), 1745-1748 (2009-03-20)
A novel approach to the synthesis of purines bearing functionalized carbon substituents or methyl in position 6 was developed. Under different reaction conditions, 6-halopurine derivatives could react with ethyl acetoacetate efficiently to yield 2-(purin-6-yl)acetoacetic acid ethyl esters, (purin-6-yl)acetates and 6-methylpurines
Hassan Valizadeh et al.
Molecular diversity, 15(1), 233-237 (2010-07-24)
In this study, a three-component one-pot synthesis of select 5-amino-6-cyano-3-hydroxybenzo[c]coumarin compounds derived from salicylaldehydes, malononitrile, and ethyl acetoacetate is reported. The reaction is conducted on grinding over MgO at room temperature resulting in good yields.
Igor R Costa et al.
Nutrients, 7(1), 1-16 (2014-12-30)
Essential amino acids (EAA) consist of a group of nine amino acids that animals are unable to synthesize via de novo pathways. Recently, it has been found that most metazoans lack the same set of enzymes responsible for the de
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