1,3-Indandione

Structural properties

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.

Preparation

1,3-Indandione was first obtained by Claisen condensation of ethyl acetate and dimethyl phthalate. A related route entails the reaction of benzoyl chloride with malonyl dichloride. It also can be obtained by oxidation of indane.

Chemical properties

The structure of the title compound has been confirmed by X-ray crystallography. Unlike some other 1,3-diketones, it does not crystallize as the enol.

The carbon at the C-2 position is alpha to both carbonyls, and thus can act as a nucleophile. It undergoes self-aldol condensation easily, resulting in bi- and triindone.

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. : : :

Uses

thumb|left|[[Diphenadione]] a commercial [[rodenticide]] derived from 1,3-indandione|130px 1,3-Indandiones with a substituent at the 2-position are potent rodenticides. Commercial products include pindone, chlorophacinone, and diphenadione. These compounds function as vitamin K antagonists, inducing hemorrhage in the affected animals.

References

References

1. [http://www.sigmaaldrich.com/catalog/product/riedel/45790?lang=en&region=US 1,3-Indandione] at [[Sigma-Aldrich]]
2. [http://www.acros.com/Ecommerce/msds.aspx?PrdNr=12209&Country=UK&Language=en MSDS] at ''Acros Organics'', retrieved on June 16, 2011
3. {{in lang. ru Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.
4. (2016). "The molecular diversity scope of 1,3-indandione in organic synthesis". Molecular Diversity.
5. (2021). "Recent advances on visible light photoinitiators of polymerization based on Indane-1,3-dione and related derivatives". European Polymer Journal.
6. (2018). "Indandione and Its Derivatives - Chemical Compounds with High Biological Potential". Mini-Reviews in Medicinal Chemistry.
7. (1887). "Ueber die Vereinigung verschiedener Ester durch Natrium". Berichte der Deutschen Chemischen Gesellschaft.
8. (2016). "The molecular diversity scope of 1,3-indandione in organic synthesis". Molecular Diversity.
9. (2008). "X-Ray structure investigation of 1,3-indandione and 1,3-dicyanomethyleneindan derivatives: A review". Crystallography Reports.
10. (2000). "Ullmann's Encyclopedia of Industrial Chemistry".