Ethyl 2,4-dioxovalerate Chemical Properties

Melting point:

16-18 °C (lit.)

Boiling point:

101-103 °C/12 mmHg (lit.)

Density 

1.126 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.474(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform, Methanol

form 

Liquid

pka

6.86±0.46(Predicted)

color 

Clear yellow

Specific Gravity

1.126

Water Solubility 

Miscible with water, ether,chloroform, methanol and ethanol.

BRN 

607062

Dielectric constant

16.1（19℃）

InChIKey

OYQVQWIASIXXRT-UHFFFAOYSA-N

CAS DataBase Reference

615-79-2(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl 2,4-dioxovalerate(615-79-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

23-24/25-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29183000

MSDS

• Language:English Provider:Ethyl 2,4-dioxovalerate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl 2,4-dioxovalerate Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

Ethyl 2,4-dioxovalerate was used in the preparation of:

• 1H-pyrazolo-[3,4-d]-pyridazin-7(6H)-one core analog
• pyrazole

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.

Synthesis

1. Sodium ethoxide (30.0 g, 0.45 mol) was slowly added to 300 mL of anhydrous ethanol under the condition of an ice-salt bath and stirred uniformly. 2. Acetone (14.7 g, 0.3 mol) was pre-mixed with diethyl oxalate (46.7 g, 0.32 mol) to form a mixed solution. 3. Under the condition of keeping the reaction temperature lower than -5° C., the above mixed solution was added to the sodium-ethanol-ethanol solution dropwise with continuous stirring for 3 hours. 4. Upon completion of the reaction, the reaction mixture was slowly poured into ice-water. 5. Add the above mixed solution dropwise to the sodium ethanolate-ethanol solution with continuous stirring for 3 h. 4. Upon completion of the reaction, the reaction mixture was slowly poured into ice water. 5. Adjust the pH of the mixture with 1 mol/L hydrochloric acid to about 4. 6. Extract the aqueous phase using ethyl acetate (EA). 7. Combine the organic layers and wash twice with 150 mL of water, followed by drying with anhydrous sodium sulfate (Na2SO4). 8. The dried organic layer was filtered and concentrated under reduced pressure to give 46.5 g of a yellow liquid product (1a) in 94% yield and 96% purity. 9. The product 1a was used directly in the subsequent reaction without further purification. 10. A similar method can be used to synthesize compounds 1b-h.

References

[1] Chemical Papers, 2017, vol. 71, # 11, p. 2053 - 2061
[2] Heterocyclic Communications, 2017, vol. 23, # 6, p. 455 - 460
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1121 - 1128
[4] Synthetic Communications, 2013, vol. 43, # 1, p. 110 - 117
[5] Monatshefte fur Chemie, 2003, vol. 134, # 9, p. 1221 - 1227

Ethyl 2,4-dioxovalerate(615-79-2)Related Product Information

• Ferric acetylacetonate
• Ethyl propiolate
• Ethanol
• Ethyl acetate
• Cupric acetylacetonate
• Ethyl pyruvate
• Acetylacetone
• Triethyl acetyl citrate
• Ethyl acrylate
• Ethylparaben
• Trinexapac-ethyl
• ZIRCONIUM(IV) ACETYLACETONATE
• Manganic acetylacetonate
• Ethyl cyanoacetate
• ISOXADIFEN-ETHYL
• Aluminum acetylacetonate
• METHYL ACETOPYRUVATE
• Nickel(II) acetylacetonate dihydrate