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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

Quality Level

200

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

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_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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Acylpyruvates as potential antifungal agents.
H A Burch
Journal of medicinal chemistry, 15(4), 429-431 (1972-04-01)
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)
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
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

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