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 to 132 °C; 264 to 270 °F; 402 to 405 K ([1][2])
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 (77 °F), 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,^[3] green,^[4] 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 at 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 other ones could be promising materials in the photonics field.

In addition, 1,3-indandione ("indanedione") is used in the first stage of forensic identification of latent finerprints. It is particularly useful for paper, and for items printed with thermal inks such as receipts. Amino acids left behind by the human hand may be developed into fingerprints by the use of it; the results, photographed with a special filter under a strong yellow-green fluorescent or green laser. It is usually the first method employed in a sequential analysis aimed at the production of evidence of a grade suitable for use in the courtroom. ^[5]

See also

• Vitamin K antagonist

References