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232564

Sigma-Aldrich

Ethyl 2,4-dioxovalerate

97%

Synonym(s):

Ethyl acetonoxalate

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About This Item

Linear Formula:
CH3COCH2COCOOC2H5
CAS Number:
615-79-2
Molecular Weight:
158.15
Beilstein/REAXYS Number:
607062
EC Number:
210-447-5
MDL number:
MFCD00009124
UNSPSC Code:
12352100
PubChem Substance ID:
24853912
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.474 (lit.)

bp

101-103 °C/12 mmHg (lit.)

mp

16-18 °C (lit.)

density

1.126 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(=O)C(=O)CC(C)=O

InChI

1S/C7H10O4/c1-3-11-7(10)6(9)4-5(2)8/h3-4H2,1-2H3

InChI key

OYQVQWIASIXXRT-UHFFFAOYSA-N

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General description

Assymmmetric hydrogenation of ethyl 2,4-dioxovalerate in the presence of chiral rhodium or ruthenium catalysts yields 2-hydroxy-4-methyltetrahydrofuran-2-one. Ethyl 2,4-dioxovalerate is a potential anti-fungal agent.

Application

Ethyl 2,4-dioxovalerate was used in the preparation of:
  • 1H-pyrazolo-[3,4-d]-pyridazin-7(6H)-one core analog
  • pyrazole

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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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John M Fevig et al.
Bioorganic & medicinal chemistry letters, 16(14), 3755-3760 (2006-05-10)
Previously, potent factor Xa inhibitors were described based on a pyrazole core. Modifications of the pyrazole core have provided additional novel, highly potent factor Xa inhibitors. This manuscript will describe the synthesis and biological activity of factor Xa inhibitors containing
Acylpyruvates as potential antifungal agents.
H A Burch
Journal of medicinal chemistry, 15(4), 429-431 (1972-04-01)
Stephen C McKeown et al.
Bioorganic & medicinal chemistry letters, 16(18), 4767-4771 (2006-07-18)
The discovery, synthesis and structure-activity relationship (SAR) of a novel series of EP1 receptor antagonists is described. Pyrazole acid 4, identified from a chemical array, had desirable physicochemical properties, an excellent in vitro microsomal inhibition and cytochrome P450 (CYP450) profile
New one pot synthesis of a chiral a-hydroxy-?-butyrolactone via sequential asymmetric hydrogenation of an a, ?-diketoester.
Blandin V, et al.
Tetrahedron Asymmetry, 9(16), 2765-2768 (1998)

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