1,3-Indandione

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
CAS Number	606-23-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:78877;
ChEMBL	ChEMBL283521 ;
ChemSpider	11322 ;
ECHA InfoCard	100.009.191
PubChem CID	11815;
UNII	4DJN7YG35G ;
CompTox Dashboard (EPA)	DTXSID2060547 ;
	InChI InChI=1S/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2 Key: UHKAJLSKXBADFT-UHFFFAOYSA-N ; InChI=1/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2 Key: UHKAJLSKXBADFT-UHFFFAOYAR;
	SMILES C1C(=O)C2=CC=CC=C2C1=O; O=C2c1ccccc1C(=O)C2;
Properties
Chemical formula	C9H6O2
Molar mass	146.145 g·mol−1
Appearance	white solid
Density	1.37 g/cm3
Melting point	129 to 132 °C (264 to 270 °F; 402 to 405 K)
Solubility in water	slight
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

1,3-Indandione (sometimes simply indanedione) is an organic compound with the molecular formula C₆H₄(CO)₂CH₂. It is a β-diketone with indane as its structural nucleus. It is a colorless or white solid, but old samples can appear yellowish^[3] or even green. It is a popular chemical scaffold (building block of various useful chemical compounds).^[4]^[5]

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.^{[citation needed]}

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.^{[citation needed]}

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.

References

^ 1,3-Indandione at Sigma-Aldrich
^ MSDS at Acros Organics, retrieved on June 16, 2011
^ (in Russian) Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.
^ Dumur, Frédéric (2021). "Recent advances on visible light photoinitiators of polymerization based on Indane-1,3-dione and related derivatives". European Polymer Journal. 143: 110178. doi:10.1016/j.eurpolymj.2020.110178. S2CID 229445473.
^ Pluskota, Robert; Koba, Marcin (2018). "Indandione and Its Derivatives - Chemical Compounds with High Biological Potential". Mini-Reviews in Medicinal Chemistry. 18 (15): 1321–1330. doi:10.2174/1389557518666180330101809. PMID 29600759. S2CID 4516564.

External links

Media related to 1,3-Indandione at Wikimedia Commons

[Sigma-1] 1,3-Indandione at Sigma-Aldrich

[Acros-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] Dumur, Frédéric (2021). "Recent advances on visible light photoinitiators of polymerization based on Indane-1,3-dione and related derivatives". European Polymer Journal. 143: 110178. doi:10.1016/j.eurpolymj.2020.110178. S2CID 229445473.

[5] Pluskota, Robert; Koba, Marcin (2018). "Indandione and Its Derivatives - Chemical Compounds with High Biological Potential". Mini-Reviews in Medicinal Chemistry. 18 (15): 1321–1330. doi:10.2174/1389557518666180330101809. PMID 29600759. S2CID 4516564.

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