1,3-Indandione

1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C9H6O2. Chemically, it is a β-diketone on an indane framework. In standard conditions it is referred to in different sources as either a colorless or yellowish,[3] green,[4] or (most commonly) yellow solid.

1,3-Indandione
Names
Preferred IUPAC name
1H-Indene-1,3(2H)-dione
Other names
Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.191
UNII
  • InChI=1S/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2 Y
    Key: UHKAJLSKXBADFT-UHFFFAOYSA-N Y
  • InChI=1/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2
    Key: UHKAJLSKXBADFT-UHFFFAOYAR
  • C1C(=O)C2=CC=CC=C2C1=O
  • O=C2c1ccccc1C(=O)C2
Properties
C9H6O2
Molar mass 146.145 g·mol−1
Appearance Yellow 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 their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Structural properties

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.

Preparation

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.

Chemical properties

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.


See also

References
  1. 1,3-Indandione at Sigma-Aldrich
  2. MSDS at Acros Organics, retrieved on June 16, 2011
  3. (in Russian) Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.
  4. Datapage Archived 2014-05-19 at the Wayback Machine, AlfaAesar, June 16, 2011
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