| Identification | More | [Name]
Ethyl 2,4-dioxovalerate | [CAS]
615-79-2 | [Synonyms]
2,4-DIOXO-PENTANOIC ACID ETHYL ESTER
AKOS MSC-0252
ETHYL 2,4-DIOXOPENTANOATE
ETHYL 2,4-DIOXOVALERATE
ETHYLACETONE OXALATE
ETHYL ACETONOXALATE
ETHYL ACETOPYRUVATE
TIMTEC-BB SBB008612
Pentanoic acid, 2,4-dioxo-, ethyl ester
Acetopyruvic acid ethyl ester
Ethylacetopyruvate,98%
Ethyl acetylpyruvate.
Ethyl (acetylmethyl)glyoxylate
Valeric acid, 2,4-dioxo-, ethyl ester
2,4-Dioxovaleric acid ethyl ester
3-Acetylpyruvic acid ethyl ester
Oxalacetone | [EINECS(EC#)]
210-447-5 | [Molecular Formula]
C7H10O4 | [MDL Number]
MFCD00009124 | [Molecular Weight]
158.15 | [MOL File]
615-79-2.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid | [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.)
| [Fp ]
>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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29183000 |
| Hazard Information | Back Directory | [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 |
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