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281492

Sigma-Aldrich

Ethyl benzoylacetate

technical grade, 90%

Synonym(s):

Benzoylacetic acid ethyl ester, Ethyl 3-oxo-3-phenylpropionate

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About This Item

Linear Formula:
C6H5COCH2COOC2H5
CAS Number:
94-02-0
Molecular Weight:
192.21
Beilstein:
389944
EC Number:
202-295-3
MDL number:
MFCD00009196
UNSPSC Code:
12352100
PubChem Substance ID:
24856975
NACRES:
NA.22

grade

technical grade

vapor density

6.6 (vs air)

Assay

90%

form

liquid

refractive index

n20/D 1.52 (lit.)

bp

265-270 °C (lit.)

solubility

alcohol: miscible
diethyl ether: miscible
water: insoluble

density

1.11 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CC(=O)c1ccccc1

InChI

1S/C11H12O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

InChI key

GKKZMYDNDDMXSE-UHFFFAOYSA-N

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General description

Ethyl benzoylacetate is an ester. It undergoes microbial reduction by bakers′ yeast (Saccharomyces cerevisiae), Beauveria sulfurescens or Geotrichum candidum to afford ethyl (S)-3-hydroxy-3-phenylpropionate. It undergoes Claisen condensation reaction with malononitrile to afford 2-cyano-5-phenyl-3,5-dioxopentanonitrile which on cyclization followed by coupling with diazonium salts yields azo derivatives.

Application

Ethyl benzoylacetate was sed in the preparation of:
  • triazipinones
  • ethyl 2-fluoro-2-benzolyacetate
  • 1,2,4-triazolo[1,5-a]pyrimidine antibiotic essramycin
  • benzo[c]furan-4,7-diones
  • iodonium ylides

Packaging

Packaged in glass bottles

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

284.0 °F - closed cup

Flash Point(C)

140 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Asymmetric synthesis of both enantiomers of fluoxetine via microbiological reduction of ethyl benzoylacetate.
Chenevert R, et al.
Tetrahedron, 48(33), 6769-6776 (1992)
Ugo Battaglia et al.
Journal of natural products, 73(11), 1938-1939 (2010-09-15)
A short synthesis of the 1,2,4-triazolo[1,5-a]pyrimidine antibiotic essramycin is described involving condensation of aminoguanidine with ethyl benzoylacetate to give an amino-1,2,4-triazole, followed by condensation with ethyl acetoacetate to form the pyrimidone ring.
Mohamed G Badrey et al.
Molecules (Basel, Switzerland), 17(10), 11538-11553 (2012-09-29)
A number of interesting heterocycles were prepared through interaction of the intermediate 3-amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno-[2,3-d]pyrimidine (1) and reagents such as hydrazonyl halides 2 to furnish triazine derivatives 4a-l. Reaction of 1 with phenacyl bromide afforded compound 5. Moreover, the title compound 1
Kuang-Po Chen et al.
Organic & biomolecular chemistry, 7(19), 4074-4081 (2009-09-19)
A manganese(III)-mediated reaction between 2-benzoyl-1,4-benzoquinones and 1,3-dicarbonyl compounds that produces benzo[c]furan-4,7-diones and anthracene-1,4-diones with high chemoselectivity is described. With ethyl butyrylacetate, by changing the solvent, benzo[c]furan-4,7-diones and anthracene-1,4-diones can be generated in high chemoselectivities. With ethyl benzoylacetate, N ,N-dimethyl acetoacetamide
The reaction of ethyl benzoylacetate with malononitrile: a novel synthesis of some pyridazine, pyridazino [2, 3-a] quinazoline and pyrrole derivatives.
Abdelrazek FM, et al.
Tetrahedron, 57(9), 1813-1817 (2001)
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