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137766

Sigma-Aldrich

Diethyl oxalpropionate

≥95%

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Synonym(s):
Diethyl 2-methyl-3-oxosuccinate, Methyloxo-butanedioic acid diethyl ester, NSC 33946
Linear Formula:
C2H5OCOCH(CH3)COCOOC2H5
CAS Number:
Molecular Weight:
202.20
Beilstein/REAXYS Number:
1783697
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95%

form

liquid

refractive index

n20/D 1.432 (lit.)

bp

138 °C/23 mmHg (lit.)

density

1.073 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(C)C(=O)C(=O)OCC

InChI

1S/C9H14O5/c1-4-13-8(11)6(3)7(10)9(12)14-5-2/h6H,4-5H2,1-3H3

InChI key

OQOCQBJWOCRPQY-UHFFFAOYSA-N

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1 of 4

This Item
T61301171263149012
Diethyl oxalpropionate ≥95%

137766

Diethyl oxalpropionate

Triethyl phosphonoacetate 98%

T61301

Triethyl phosphonoacetate

Diethyl oxalacetate sodium salt 95%

171263

Diethyl oxalacetate sodium salt

Dimethyl suberate 99%

149012

Dimethyl suberate

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

refractive index

n20/D 1.432 (lit.)

refractive index

n20/D 1.431 (lit.)

refractive index

-

refractive index

n20/D 1.432 (lit.)

bp

138 °C/23 mmHg (lit.)

bp

142-145 °C/9 mmHg (lit.)

bp

-

bp

268 °C (lit.)

form

liquid

form

-

form

-

form

liquid

density

1.073 g/mL at 25 °C (lit.)

density

1.13 g/mL at 25 °C (lit.)

density

-

density

1.014 g/mL at 25 °C (lit.)

Application

Diethyl oxalpropionate was used in the synthesis of 2-hydroxy-3-methylsuccinic acid. It was used as starting reagent in the synthesis of racemic 4-alkyloxycarbonyl-3,3-dimethyl-2-oxetanones and 4-quinolinone 2-carboxylic acid.
Reactant involved in:
  • Synthesis of anticancer and antiviral agents
  • Oxidation by organohypervalent iodine reagent
  • Synthesis of monomers for preparation of functional polyesters
  • Synthesis of calpain inhibitors
  • Preparation of human A2A receptor antagonists
  • Structural studies of dihydropteroate synthase inhibitors

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

206.6 °F - closed cup

flash_point_c

97 °C - closed cup

ppe

Eyeshields, Gloves


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Dong Hyuk Nam et al.
Bioorganic & medicinal chemistry letters, 18(1), 205-209 (2007-11-21)
Calpains are involved in a variety of calcium-regulated cellular processes, such as signal transduction, cell proliferation, differentiation, and apoptosis. Excessive calpain activation contributes to serious cellular damage and has been reported in many pathological conditions. 4-Quinolinone 2-carboxamide derivatives were prepared
Synthesis of New Homopolyester and Copolyesters by Anionic Ring-opening Polymerization of a, a', ?-Trisubstituted ?-Lactones.
Barbaud C, et al.
Macromolecular Chemistry and Physics, 205(2), 199-207 (2004)
Leanne A Pearson et al.
The Journal of biological chemistry, 282(7), 4681-4692 (2006-12-05)
The cyanobacterium Microcystis aeruginosa is widely known for its production of the potent hepatotoxin microcystin. This cyclic heptapeptide is synthesized non-ribosomally by the thio-template function of a large modular enzyme complex encoded within the 55-kb microcystin synthetase gene (mcy) cluster.

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