Acetonylmalonic acid diethyl ester
- CAS No.
- 23193-18-2
- Chemical Name:
- Acetonylmalonic acid diethyl ester
- Synonyms
- DIETHYL ACETONYLMALONATE;DIETHYL 2-OXOPROPYLMALONATE;Diethyl Acetonylmalonate >Diethyl 2-(2-oxopropyl)Malonate;ethyl 2-carbethoxy-4-oxo-valerate;Acetonylmalonic acid diethyl ester;diethyl 2-(2-oxopropyl)propanedioate;2-OXOPROPYLMALONIC ACID DIETHYL ESTER;1,3-diethyl 2-(2-oxopropyl)propanedioate;2-Oxopropylmalonic acid eiethyl ester
- CBNumber:
- CB5459968
- Molecular Formula:
- C10H16O5
- Molecular Weight:
- 216.23
- MDL Number:
- MFCD00177949
- MOL File:
- 23193-18-2.mol
- MSDS File:
- SDS
Acetonylmalonic acid diethyl ester price More Price(10)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| TCI Chemical | A1503 | Diethyl Acetonylmalonate >95.0%(GC) | 23193-18-2 | 1g | $31 | 2026-04-30 | Buy |
| TCI Chemical | A1503 | Diethyl Acetonylmalonate >95.0%(GC) | 23193-18-2 | 5g | $94 | 2026-04-30 | Buy |
| aablocks | AA003NKN | Acetonylmalonic acid diethyl ester >95.0%(GC) | 23193-18-2 | 1g | $25 | 2026-05-28 | Buy |
| aablocks | AA003NKN | Acetonylmalonic acid diethyl ester >95.0%(GC) | 23193-18-2 | 5g | $76 | 2026-05-28 | Buy |
| Crysdot | CD13017733 | Diethyl 2-(2-oxopropyl)malonate 95+% | 23193-18-2 | 1g | $95 | 2026-05-27 | Buy |
Acetonylmalonic acid diethyl ester Chemical Properties, Uses, Production
Uses
Diethyl Acetonylmalonate is a doubly functionalized reagent, the ketone acting as an internal trapping agent after the reaction of the malonate anion; for synthesis of five-membered rings.
Synthesis Reference(s)
The Journal of Organic Chemistry, 46, p. 4631, 1981 DOI: 10.1021/jo00335a084
Synthesis
A detailed procedure reports the alkylation of Diethyl Malonate by chloroacetone on a 100 g scale, giving diethyl acetonylmalonate (1) with a yield of 55% after distillation. Since chloroacetone is toxic and highly irritating to the eyes, skin, and mucous membranes, an alternative procedure using Isopropenyl Acetate, a mild irritant and a much less toxic compound than chloroacetone, should be seriously considered. Thus the reaction of dimethyl malonate with isopropenyl acetate in the presence of Cerium(IV) Ammonium Nitrate (CAN) followed by a mild basic treatment affords dimethyl acetonylmalonate in a yield of 82% on a 5-10 g scale (eq 1). This procedure offers advantages regarding the yield and reaction conditions, and it uses available starting materials.
References
1. Mercier C.; Addas A. R.; Deslongchamps P. CJC 1972, 50, 1882.
2. The Merck Index, 11th ed.; Merck: Rahway, NJ, 1989.
3. Baciocchi E.; Civitarese G.; Ruzziconi R. TL 1987, 28, 5357.
Acetonylmalonic acid diethyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
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