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281492

Ethyl benzoylacetate

Name: Ethyl benzoylacetate
Brand: ALDRICH

technical grade, 90%

Synonyme(s) :

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

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About This Item

Formule linéaire :

C₆H₅COCH₂COOC₂H₅

Numéro CAS:

94-02-0

Poids moléculaire :

192.21

Numéro Beilstein :

389944

Numéro CE :

202-295-3

Numéro MDL:

MFCD00009196

Code UNSPSC :

12352100

ID de substance PubChem :

24856975

Nomenclature NACRES :

NA.22

Qualité

technical grade

Densité de vapeur

6.6 (vs air)

Pureté

90%

Forme

liquid

Indice de réfraction

n20/D 1.52 (lit.)

Point d'ébullition

265-270 °C (lit.)

Solubilité

alcohol: miscible
diethyl ether: miscible
water: insoluble

Densité

1.11 g/mL at 25 °C (lit.)

Chaîne SMILES

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

Clé InChI

GKKZMYDNDDMXSE-UHFFFAOYSA-N

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Catégories apparentées

Synthons (building blocks)

Synthons organiques

Description générale

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

Conditionnement

Packaged in glass bottles

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

284.0 °F - closed cup

Point d'éclair (°C)

140 °C - closed cup

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Ethyl acetoacetate

A short synthesis of the triazolopyrimidine antibiotic essramycin.

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.

Asymmetric synthesis of both enantiomers of fluoxetine via microbiological reduction of ethyl benzoylacetate.

Chenevert R, et al.

Tetrahedron, 48(33), 6769-6776 (1992)

3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d]pyrimidine: an effecient key precursor for novel synthesis of some interesting triazines and triazepines as potential anti-tumor agents.

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

Free radical reaction between 2-benzoyl-1,4-benzoquinones and 1,3-dicarbonyl compounds.

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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