DIETHYL OXALPROPIONATE Chemical Properties

Boiling point:

138 °C/23 mmHg (lit.)

Density 

1.073 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.432(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Hexane (Slightly), Methanol (Slightly)

form 

Oil

pka

9.30±0.46(Predicted)

color 

Clear Colourless to Pale Yellow

BRN 

1783697

InChI

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

InChIKey

OQOCQBJWOCRPQY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

759-65-9(CAS DataBase Reference)

EPA Substance Registry System

Butanedioic acid, methyloxo-, diethyl ester (759-65-9)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

HS Code 

2917198090

MSDS

• Language:English Provider:SigmaAldrich

DIETHYL OXALPROPIONATE Usage And Synthesis

Uses

Reactant involved in:• ;Synthesis of anticancer and antiviral agents1• ;Oxidation by organohypervalent iodine reagent2• ;Synthesis of monomers for preparation of functional polyesters3• ;Synthesis of calpain inhibitors4• ;Preparation of human A2A receptor antagonists5• ;Structural studies of dihydropteroate synthase inhibitors6

Uses

Diethyl Oxalopropionate is a useful precursor in the synthesis of 2-Methylcitric Acid (M265080); a metabolite of Citric Acid (C521000) that can also be formed from condensation of propionoyl-CoA and oxaloacetic acid catalyzed by a citrate synthase enzyme.

Uses

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

Definition

ChEBI: Diethyl 2-methyl-3-oxosuccinate is an alpha-ketoester, a beta-ketoester, an ethyl ester and a diester.

Synthesis

At room temperature, diethyl oxalate (300 g, 2.94 mol) and ethyl propionate (429.4 g, 2.94 mol) were dissolved in 1.8 L of anhydrous ethanol, followed by the addition of sodium ethoxide (300 g, 4.41 mol). The reaction mixture was stirred overnight. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted to 7 with 6 N hydrochloric acid. subsequently, the mixture was concentrated under reduced pressure to remove the solvent. The concentrated residue was diluted with water and extracted with ethyl acetate. The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give diethyl oxalylpropionate (400 g, 67% yield) as a red liquid, which could be used in subsequent steps without further purification.1H NMR (400 MHz, CDCl3) δ ppm: 4.103-4.386 (m, 5H); 1.246-1.439 (m, 9H) .

References

[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9701 - 9708
[2] Patent: US2015/25087, 2015, A1. Location in patent: Paragraph 0168; 0237; 0238
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 132
[4] Justus Liebigs Annalen der Chemie, 1888, vol. 246, p. 329
[5] Journal of the Chemical Society, 1924, vol. 125, p. 313

DIETHYL OXALPROPIONATE(759-65-9)Related Product Information

• Diethyl oxalacetate
• Diethyl succinate
• Methyl pyruvate
• DIETHYL OXALPROPIONATE
• 3-CHLORO-2-METHYLBENZYLAMINE
• Methyl 2-oxoacetate
• MONO-METHYL SUCCINATE
• Ethyl acetoacetate
• Ethyl 3-methyl-2-oxobutyrate
• Methyl 4-methoxybutanoate
• Ethyl 3-oxobutanoate sodium salt
• Ethyl 2-methylacetoacetate
• Pyruvic acid
• MONO-ETHYL SUCCINATE
• Ethyl pyruvate
• ETHYL 4-METHOXY-3-OXO-BUTANOATE
• Methyl 4-methoxyacetoacetate
• Oxaloacetic acid