Diethyl oxomalonate
| Names | |
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| Preferred IUPAC name
Diethyl oxopropanedioate | |
| Other names
Diethyl mesoxalate; Ethyl ketomalonate; Diethyl ketomalonate
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.009.252 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H10O5 | |
| Molar mass | 174.152 g·mol−1 |
| Appearance | Clear colorless to yellow liquid |
| Density | 1.142 g/cm3 |
| Melting point | −30 °C (−22 °F; 243 K) |
| Boiling point | 208–210 °C (406–410 °F; 481–483 K) 96–97 °C (12 mmHg) |
| Highly soluble | |
| Solubility in ethanol, diethylether, chloroform | Soluble |
| Hazards | |
| GHS labelling:[1] | |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Diethyl oxomalonate is the diethyl ester of mesoxalic acid (ketomalonic acid), the simplest oxodicarboxylic acid and thus the first member (n = 0) of a homologous series HOOC–CO–(CH2)n–COOH with the higher homologues oxalacetic acid (n = 1), α-ketoglutaric acid (n = 2) and α-ketoadipic acid (n = 3) (the latter a metabolite of the amino acid lysine). Diethyl oxomalonate reacts because of its highly polarized keto group as electrophile in addition reactions and is a highly active reactant in pericyclic reactions such as the Diels-Alder reactions, cycloadditions or ene reactions. At humid air, mesoxalic acid diethyl ester reacts with water to give diethyl mesoxalate hydrate and the green-yellow oil are spontaneously converted to white crystals.