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| Names | |
|---|---|
| Preferred IUPAC name 1H-Indene-1,3(2H)-dione | |
| Other names Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.009.191 |
| UNII | |
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| Properties | |
| C9H6O2 | |
| Molar mass | 146.145 g·mol−1 |
| Appearance | white solid |
| Density | 1.37 g/cm3 |
| Melting point | 129 to 132 °C (264 to 270 °F; 402 to 405 K)[1][2] |
| slight | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1,3-Indandione (sometimes simplyindanedione) is anorganic compound with the molecular formula C6H4(CO)2CH2. It is aβ-diketone withindane as its structural nucleus. It is a colorless or white solid, but old samples can appear yellowish[3] or even green. It is a popularchemical scaffold (building block of various useful chemical compounds).[4][5]
Solid 1,3-indandione is a diketone, As a solution in water, it is partially (~2%) enolized. The enolate anion exhibits significant delocalization, and the highest electron density is on the second carbon. This acid-base behavior explains many properties of the compound.[citation needed]
1,3-Indandione can be prepared bydecarboxylation of the sodium salt of 2-ethoxycarbonyl-1,3-indandione, which itself is obtained byClaisen condensation ofethyl acetate anddimethyl phthalate.[citation needed]
The carbon at the C-2 position isalpha to bothcarbonyls, and thus can act as anucleophile. It undergoes self-aldol condensation quite easily, resulting inbindone.
Bromination occurs at the 2-position:
One or both carbonyl groups can bereduced toalcohol groups ormethylene groups, depending on the method used.
Media related to1,3-Indandione at Wikimedia Commons
