From Wikipedia, the free encyclopedia
Jump to: navigation, search
Skeletal formula
Ball-and-stick model
IUPAC name
Other names
Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione
606-23-5 YesY
ChEMBL ChEMBL283521 YesY
ChemSpider 11322 YesY
Jmol-3D images Image
PubChem 11815
Molar mass 146.14 g·mol−1
Appearance Yellow solid
Density 1.37 g / cm3
Melting point 129 °C (264 °F; 402 K)[1][2]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

1,3-Indandione is an aromatic trans-fixed β-diketone. In standard conditions it is referred to in different sources as either a colorless or yellowish,[3] green,[4] or (most commonly) yellow solid.

Structural properties[edit]

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.


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.

NaECI preparation.svg

Chemical properties[edit]

1,3-Indandione is a very strong C-nucleophile. It undergoes self-condensation quite easily, resulting in bindone.


Bromination occurs at the 2-position:

Bromination 1,3-Indanediol.svg

1,3-Indandione could be reduced to indanone, 3-hydroxy-1-indanone, 1,3-indanediol or even indane, depending on the method used.

Partial Reduction 1,3-Indanedione.svg
Reduction 1,3-Indanedione.svg


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

In addition, 1,2-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[edit]


  1. ^ 1,3-Indandione at Sigma-Aldrich
  2. ^ MSDS at Acros Organics, retrieved on June 16, 2011
  3. ^ (Russian) Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.
  4. ^ Datapage, AlfaAesar, June 16, 2011
  5. ^ Sequential Processing 2010 : 01 : History of Indanedione. Sequential Processing of Documents For Fingerprints (NFSTC). Retrieved August 2, 2013.