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689963

Sigma-Aldrich

Ethyl benzoylacetate

Arxada quality, ≥98% (GC)

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/REAXYS Number:
389944
EC Number:
202-295-3
MDL number:
MFCD00009196
UNSPSC Code:
12352100
PubChem Substance ID:
329761302
NACRES:
NA.22

vapor density

6.6 (vs air)

assay

≥98% (GC)

form

liquid

quality

Arxada quality

manufacturer/tradename

Arxada AG

refractive index

n20/D 1.52 (lit.)

bp

265-270 °C (lit.)

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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Application

Ethyl benzoylacetate is a general reagent used in the synthesis of substituted pyrroles, oxazoles, indoles, imidazo[1, 2-a] pyridines and a variety of other aromatic compounds.

Storage Class

10 - Combustible liquids

wgk_germany

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)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1317
BCCB3552
BCBZ6330
BCBR5553V
BCBP9812V

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Ethyl acetoacetate Arxada quality, ≥99.0% (GC)

Sigma-Aldrich

688983

Ethyl acetoacetate

Facile access to polysubstituted indoles via a cascade Cu-catalyzed arylation? condensation process.
Chen Y, et al.
The Journal of Organic Chemistry, 72(24), 9329-9334 (2007)
Facile synthesis of polysubstituted oxazoles via a copper-catalyzed tandem oxidative cyclization.
Wan C, et al.
Organic Letters, 12(10), 2338-2341 (2010)
Rhenium-and manganese-catalyzed synthesis of aromatic compounds from 1, 3-dicarbonyl compounds and alkynes.
Kuninobu Y, et al.
The Journal of Organic Chemistry, 75(2), 334-341 (2009)
TBAI-catalyzed oxidative coupling of aminopyridines with β-keto esters and 1, 3-diones?synthesis of imidazo [1, 2-a] pyridines.
Ma L, et al.
Chemical Communications (Cambridge, England), 47(40), 11333-11335 (2011)
Expedient synthesis of highly substituted pyrroles via tandem rearrangement of α-diazo oxime ethers.
Jiang Y, et al.
Journal of the American Chemical Society, 134(9), 4104-4107 (2012)

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