Acetonedicarboxylic acid
Chemical compound
From Wikipedia, the free encyclopedia
Acetonedicarboxylic acid is the organic compound with the formula O=C(CH2CO2H)2. It is classified as both a dicarboxylic acid and an oxocarboxylic acid.[2]
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| Names | |
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| Preferred IUPAC name
3-Oxopentanedioic acid | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.999 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C5H6O5 | |
| Molar mass | 146.09814 g/mol |
| Appearance | colorless or white solid |
| Density | 1.499 g/cm3 |
| Melting point | 122 °C (252 °F; 395 K) (decomposes) |
| Boiling point | 408.4 °C (767.1 °F; 681.5 K) (760mm Hg) |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
| Flash point | 214.9 °C (418.8 °F; 488.0 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
Acetonedicarboxylic acid is prepared commercially by oxidation of citric acid.[2] It can also be prepared by treating citric acid with fuming sulfuric acid.[3]
Reactions and uses
Upon heating it undergoes decarboxylation first to give acetoacetic acid then acetone:[2]
- O=C(CH2CO2H → O=C(CH3)(CO2H) + CO2
- O=C(CH3)(CO2H) → O=C(CH3)2 + CO2
Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocycles[4] One example is it use in Robinson's classic synthesis of tropinone. It participates in the Weiss–Cook reaction.[5]