1,3-Indandione

1,3-Indandione
IUPAC name indane-1,3-dione
Other names Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione
Identifiers
CAS number	606-23-5 Y
PubChem	11815
ChemSpider	11322 Y
ChEMBL	CHEMBL283521 Y
Jmol-3D images	Image 1 Image 2
SMILES C1C(=O)C2=CC=CC=C2C1=O O=C2c1ccccc1C(=O)C2
InChI 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
Properties
Molecular formula	C9H6O2
Molar mass	146.14 g mol−1
Appearance	Yellow solid
Density	1.37 g / cm3
Melting point	129-132 °C, 402-405 K, 264-270 °F ()
Solubility in water	slight
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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, green, or (most commonly) yellow solid.

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-etoxycarbonyl-1,3-indandione, which itself is obtained by Claisen condensation of ethyl acetate and dimethyl phthalate.

Chemical properties

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.

Uses

Certain derivatives are used in human medicine. Some another ones could be promising materials in the photonics field.

See also

• Vitamin K antagonist