| Identification | More | [Name]
Diethyl ketomalonate | [CAS]
609-09-6 | [Synonyms]
DIETHYL KETOMALONATE
DIETHYL MESOXALATE
DIETHYL MESOXYLATE
DIETHYL OXOMALONATE
ETHYL OXOMALONATE
KETOMALONIC ACID DIETHYL ESTER
MESOXALIC ACID DIETHYL ESTER
Diethyl 2-oxomalonate
Ethyl mesoxalate
oxo-propanedioicacidiethylester
Diethyl ketomalonate, (Diethyl mesoxalate
Diethyl mesoxalate~Diethyl oxomalonate~Oxopropanedioic acid diethyl ester
2-Oxomalonic acid diethyl ester
DiethylKetomaloante
Diethylmesoxalate=Diethyloxomalonate
Diethylketomalonate,95%
Diethyl ketomalonate 97%
Diethyl mesoxalate, Ketomalonic acid diethyl ester
Diethyl ketomalonate, Ketomalonic acid diethyl ester
2-Oxopropanedioic acid diethyl | [EINECS(EC#)]
210-176-2 | [Molecular Formula]
C7H10O5 | [MDL Number]
MFCD00009121 | [Molecular Weight]
174.15 | [MOL File]
609-09-6.mol |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P271-P280 | [Hazard Codes ]
Xi | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
21 | [Hazard Note ]
Irritant | [TSCA ]
T | [HazardClass ]
IRRITANT, MOISTURE SENSITIVE | [HS Code ]
29183000 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear yellow liquid | [Uses]
Diethyl ketomalonate, reagent employed in Wittig and Aza-Wittig reactions for synthesis of triazoles, and 2-azadienes, respectively. | [Application]
Diethyl ketomalonate can be used in electron-deficient heterodienophile; Diels-Alder reaction; heterodipolarophile; [3 + 2] cycloaddition; 1,3-diyl trapping agent; 1,4-dipolar cycloaddition; [2 + 2] cycloaddition; enophile; ene reaction; electrophilic addition; Wittig reactions; condensation with amines; Pictet-Spengler reactions. | [Preparation]
Diethyl ketomalonate can be prepared by bromination of Diethyl Malonate to the dibromomalonic ester, exchange of one bromine atom for acetate and α-elimination of acetyl bromide. Alternatively, diethyl malonate is condensed with benzaldehyde to afford the Knoevenagel product which is cleaved by ozonolysis. | [Synthesis Reference(s)]
Synthetic Communications, 24, p. 695, 1994 DOI: 10.1080/00397919408012648
The Journal of Organic Chemistry, 46, p. 2598, 1981 DOI: 10.1021/jo00325a039 | [Synthesis]
The general procedure for the synthesis of diethyl ketomalonate from diethyl methylidenemalonate was as follows: 258 g of diethyl methylidenemalonate prepared by Knoevenagel condensation reaction of malonic acid and formaldehyde was dissolved in 1 liter of methanol, followed by ozonation reaction. Upon completion of the reaction, 5 g of 10% Pd-on-C was added as a hydrogenation catalyst and placed in 200 ml of methanol to carry out the hydrogenation reaction, with a hydrogen consumption of 28.9 standard liters (86% of the theoretical value was reached). The reaction mixture was post-treated according to the method of Example 5 and subsequently concentrated under vacuum to give 214 g of diethyl ketomalonate with a boiling point of 10.0-112°C/20 mmHg in 82% yield of the theoretical value. | [storage]
Diethyl ketomalonate is stable for at least 6 months if stored in the refrigerator. | [References]
[1] Patent: US4769464, 1988, A
[2] Tetrahedron Letters, 1981, vol. 22, # 46, p. 4607 - 4610 |
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