1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C6H4(CO)2CH2. It is a β-diketone with indane as its structural nucleus. It is a colorless or white solid, but old samples can appear yellowish[3] or even green. It is a popular chemical scaffold (building block of various useful chemical compounds).[4][5]
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Preferred IUPAC name
1H-Indene-1,3(2H)-dione | |
Other names
Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione
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ECHA InfoCard | 100.009.191 |
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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] |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 by decarboxylation of the sodium salt of 2-ethoxycarbonyl-1,3-indandione, which itself is obtained by Claisen condensation of ethyl acetate and dimethyl phthalate.[citation needed]
The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation quite easily, resulting in bindone.
Bromination occurs at the 2-position:
One or both carbonyl groups can be reduced to alcohol groups or methylene groups, depending on the method used.