| 1,3-Indandione | |
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indane-1,3-dione |
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Other names
Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione |
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| Identifiers | |
| CAS number | 606-23-5 |
| PubChem | 11815 |
| ChemSpider | 11322 |
| ChEMBL | CHEMBL283521 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C9H6O2 |
| Molar mass | 146.14 g mol−1 |
| Appearance | Yellow solid |
| Density | 1.37 g / cm3 |
| Melting point | |
| Solubility in water | slight |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
1,3-Indandione is an aromatic trans-fixed β-diketone. In standard conditions it is referred to in different sources as either colorless or yellowish,[3] green,[4] or (most commonly) yellow solid.
Contents |
In the solid state, 1,3-indandione occurs as a diketone; in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density is on the second carbon. This explains many of chemical properties of the compound.
1,3-Indandione can be prepared by decarboxylation of the sodium salt of 2-etoxycarbonyl-1,3-indandione, which itself is obtained by Claisen condensation of ethyl acetate and dimethyl phthalate.
1,3-Indandione is a very strong C-nucleophile. It undergoes self-condensation quite easily, resulting in bindone.
Bromination occurs a the 2-position:
1,3-Indandione could be reduced to indanone, 3-hydroxy-1-indanone, 1,3-indanediol or even indane, depending on the method used.
Certain derivatives are used in human medicine. Some another ones could be promising materials in the photonics field.
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