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137766

Sigma-Aldrich

Diethyl oxalpropionate

≥95%

Synonym(s):

Diethyl 2-methyl-3-oxosuccinate, Methyloxo-butanedioic acid diethyl ester, NSC 33946

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About This Item

Linear Formula:
C2H5OCOCH(CH3)COCOOC2H5
CAS Number:
759-65-9
Molecular Weight:
202.20
Beilstein:
1783697
EC Number:
212-071-7
MDL number:
MFCD00009163
UNSPSC Code:
12352100
PubChem Substance ID:
24848348
NACRES:
NA.22

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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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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

206.6 °F - closed cup

Flash Point(C)

97 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), 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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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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