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1,3-Indandione

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1,3-Indandione
Names
IUPAC name
indane-1,3-dione
Other names
Indandione

1,3-diketohydrindene
1,3-dioxoindane

1,3-hydrindendione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.191 Edit this at Wikidata
  • 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 146.14 g/mol
Appearance yellow solid
Density 1.37 g / cm3
Melting point 129—132[1][2] °C
slight
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

1,3-indandione is an aromatic trans-fixed β-diketone, in standard conditions it is referred to in different sources as colourless or yellowish[3], green[4] or (most commonly) yellow solid. It is an anticoagulant used as a rodenticide.[citation needed]

A valuable contribution in research of 1,3-indandiones and other diketones belongs to a great Latvian chemist Gustavs Vanags.

Structural properties

In the solid 1,3-indandione occurs as a diketone whereas its water solution is partially (~2%) enolized. The enolate anion exhibits significant delocalisation, and the highest electron density is on the second carbon. This explains many of chemical properties of the compound.

Preparation

The well-known method is decarboxilation of the sodium salt of 2-etoxycarbonyl-1,3-indandione, which itself is obtained by Claisen condensation of ethyl acetate and diethyl phthalate (of course another alcohol moieties can be present in the raw materials).

Chemical properties

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

Another example is bromination.

1,3-indandione could be reduced till indanone, 3-hydroxy-1-insanone, 1,3-indanediol or even indane, depending on the method used.

Uses

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

See also

References

  1. ^ Sigma-Aldrich|ALDRICH|I2002|Date=October 20 2010}}
  2. ^ MSDS at Acros Organics, retrieved on June 16 2011
  3. ^ Template:Ref-ru Нейланд О. Я. Органическая химия: Учеб. для хим. спец. вузов. Москва: Высшая школа, 1990.— с. 481—490.
  4. ^ Alfa|L01584|Date=June 16 2011}}



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