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Merck
CN

281492

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24856975
EC Number:
202-295-3
Beilstein/REAXYS Number:
389944
MDL number:
MFCD00009196
Assay:
90%
Form:
liquid

Key Documents

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Product Name

Ethyl benzoylacetate, technical grade, 90%

InChI key

GKKZMYDNDDMXSE-UHFFFAOYSA-N

InChI

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

SMILES string

CCOC(=O)CC(=O)c1ccccc1

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.)

functional group

ester
ketone
phenyl

Quality Level

100

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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

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.

Packaging

Packaged in glass bottles

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

284.0 °F - closed cup

flash_point_c

140 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB5711
STBL1731
STBK0257
STBJ6759
STBJ2493

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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
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
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.
Tsugio Kitamura et al.
Organic letters, 13(9), 2392-2394 (2011-04-09)
A simple, practical, and convenient fluorination of 1,3-dicarbonyl compounds was achieved by direct use of aqueous hydrofluoric acid and iodosylbenzene (PhIO). The reaction of ethyl benzoylacetate with the reagent system of aqueous HF and PhIO in CH(2)Cl(2) gave ethyl 2-fluoro-2-benzolyacetate
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