1,3-Indandione

1,3-Indandione
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
1H-Indene-1,3(2H)-dione
Other names
Indandione; 1,3-Diketohydrindene; 1,3-Dioxoindane; 1,3-Hydrindendione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.191 Edit this at Wikidata
UNII
  • InChI=1S/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2 checkY
    Key: UHKAJLSKXBADFT-UHFFFAOYSA-N checkY
  • InChI=1/C9H6O2/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4H,5H2
    Key: UHKAJLSKXBADFT-UHFFFAOYAR
  • C1C(=O)C2=CC=CC=C2C1=O
  • O=C2c1ccccc1C(=O)C2
Properties
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)[1][2]
slight
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.


See also

References

  1. ^ 1,3-Indandione at Sigma-Aldrich
  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.