ChemicalBook > CAS DataBase List > Diethyl ketomalonate
Diethyl ketomalonate
- Product Name
- Diethyl ketomalonate
- CAS No.
- 609-09-6
- Chemical Name
- Diethyl ketomalonate
- Synonyms
- Diethyl 2-oxomalonate;DIETHYL MESOXALATE;diethyl 2-oxopropanedioate;1,3-diethyl 2-oxopropanedioate;ketomaL;Keto Malonate;Ethyl mesoxalate;ETHYL OXOMALONATE;DIETHYL MESOXYLATE;Diethyl ketomalote
- CBNumber
- CB0224840
- Molecular Formula
- C7H10O5
- Formula Weight
- 174.15
- MOL File
- 609-09-6.mol
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Diethyl ketomalonate Property
- Melting point:
- -70°C
- Boiling point:
- 208-210 °C (lit.)
- Density
- 1.142 g/mL at 25 °C (lit.)
- refractive index
- n20/D 1.415
- Flash point:
- >230 °F
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Slightly), Methanol
- form
- liquid
- color
- green-yellow
- Specific Gravity
- 1.142
- Water Solubility
- Fully miscible with water.
- Sensitive
- Moisture Sensitive
- Merck
- 14,5913
- BRN
- 971873
- InChIKey
- DBKKFIIYQGGHJO-UHFFFAOYSA-N
- CAS DataBase Reference
- 609-09-6(CAS DataBase Reference)
- NIST Chemistry Reference
- Propanedioic acid, oxo-, diethyl ester(609-09-6)
- EPA Substance Registry System
- Propanedioic acid, oxo-, diethyl ester (609-09-6)
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Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
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N-Bromosuccinimide Price
Sigma-Aldrich
- Product number
- D97401
- Product name
- Diethyl ketomalonate
- Purity
- 95%
- Packaging
- 5g
- Price
- $58.3
- Updated
- 2025/07/31
Sigma-Aldrich
- Product number
- D97401
- Product name
- Diethyl ketomalonate
- Purity
- 95%
- Packaging
- 25g
- Price
- $181.45
- Updated
- 2025/07/31
TCI Chemical
- Product number
- M0866
- Product name
- Diethyl Mesoxalate
- Purity
- >94.0%(GC)
- Packaging
- 5g
- Price
- $55
- Updated
- 2025/07/31
TCI Chemical
- Product number
- M0866
- Product name
- Diethyl Mesoxalate
- Purity
- >94.0%(GC)
- Packaging
- 25g
- Price
- $218
- Updated
- 2025/07/31
TRC
- Product number
- D476633
- Product name
- Diethyl ketomalonate
- Packaging
- 1g
- Price
- $85
- Updated
- 2021/12/16
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Diethyl ketomalonate Chemical Properties,Usage,Production
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
3377-20-6
609-09-6
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
Diethyl ketomalonate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Diethyl ketomalonate manufacturers
Hebei Chuanghai Biotechnology Co., Ltd
- Product
- Diethyl ketomalonate 609-09-6
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100 mt
- Release date
- 2024-11-13
Honest Joy Holdings Limited
- Product
- Diethyl ketomalonate 609-09-6
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98.7%
- Supply Ability
- 100 tons
- Release date
- 2022-02-18
Zhuozhou Wenxi import and Export Co., Ltd
- Product
- Diethyl ketomalonate 609-09-6
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-08-11
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