Merck
CN
All Photos(1)

Documents

Safety Information

281492

Sigma-Aldrich

Ethyl benzoylacetate

technical grade, 90%

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
Benzoylacetic acid ethyl ester, Ethyl 3-oxo-3-phenylpropionate
Linear Formula:
C6H5COCH2COOC2H5
CAS Number:
94-02-0
Molecular Weight:
192.21
Beilstein:
389944
EC Number:
202-295-3
MDL number:
MFCD00009196
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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Regulatory Information

新产品

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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Asymmetric synthesis of both enantiomers of fluoxetine via microbiological reduction of ethyl benzoylacetate.
Chenevert R, et al.
Tetrahedron, 48(33), 6769-6776 (1992)
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
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.
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service