1,3-Indandione

Yellow powder

Fixed

1.37 g · cm -3

129-132 ° C

• 0.864 Pa ( 322.95 K)
• 23.543 Pa ( 357.71 K)

7.2 ( 18 ° C)

Slightly soluble in water

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1,3 - indandione is a diketone from the group of bicyclic aromatic hydrocarbons.

Production and representation

1,3- indandione can be obtained by a Claisen condensation with diethyl phthalate or dibutyl phthalate as a starting material, followed by hydrolysis and decarboxylation.

The synthesis of 1,3 - indanedione also through one of the Diels -Alder reaction similar reaction between o -xylylene, and 4- cyclopentene -1 ,3- dione possible.

Oxidation of indane with oxidizing agents such as Hydrogen peroxide or tert- butyl hydroperoxide proceeds only with poor yields, as the main product produced thereby 1- indanone.

Properties

Physical Properties

The enthalpy of formation of 1,3- indanedione in the gas phase at 298.15 K is 165.0 ± 2.6 kJ / mol and the heat of fusion of 17.2 kJ / mol, and the enthalpy of vaporization 72.6 kJ / mol.

Chemical Properties

In the 1,3 - indanedione molecule is a keto -enol tautomerism ago

Bromination of 1,3- indanedione to 2 -bromo -1 ,3- indandione (CAS 7319-63-3, mp 118-120 ° C) passes through the enol form, with elimination of hydrogen bromide. A further bromination to 2,2-dibromo- 1 ,3- indandione (melting point 181-182 ° C) passes by the same mechanism via the enol form of Monobromderivats.

The reduction of 1,3 - indanedione by Clemmensen with amalgamated zinc in hydrochloric acid leads to the indane. As a byproduct indene.

Catalytic hydrogenation with ionic triethylsilane and trifluoroacetic acid also leads to indane.

The reduction is performed with sodium borohydride and palladium as a catalyst, the reduction proceeds only until the 3-hydroxy -1-indanone, and subsequently the 1,3 - Indandiol.

The reduction with zinc dust in glacial acetic acid provides the 3-hydroxy -1-indanone.

Use

1,3 - indanedione can be further processed ( a rodenticide ) by reaction with 1,1- diphenylacetone to diphacinone.

1,3 - indanedione can be used in addition to 1 - indanone and 2-indanone as a starting material for the production of ninhydrin. Other reagents as N-bromosuccinimide and dimethyl sulfoxide can be used.

Related compounds

• Indane
• Indene
• Diphacinone
• Chlordane
• Chlorphacinon