Tropolone

Chemical properties

White to light yellow crystalline

The Uses of Tropolone

Tropolone is a sensitive reagent for reducing sugars. A non-benzenoid aromatic compound, Reagent for the preparation of fused heterocycles and complexes of Ga(III) and In(III).

The Uses of Tropolone

Reagent for the preparation of fused heterocycles1 and complexes of Ga(III) and In(III).2 Used as medicine and dye intermediates.

What are the applications of Application

Tropolone is a reagent for the preparation of fused heterocycles and complexes of Ga(III) and In(III)

Definition

ChEBI: Tropolone is a cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii. It has a role as a bacterial metabolite, a toxin and a fungicide. It is a cyclic ketone, an enol and an alpha-hydroxy ketone. It derives from a hydride of a cyclohepta-1,3,5-triene.

Flammability and Explosibility

Not classified

Synthesis

To a mixture of sodium hydroxide (33 g) with glacial acetic acid (270 ml) was added dropwise via funnel 7,7-dichlorobicyclo[3,2,0]hepta-2-ene-6-ketone (33.5 g) under nitrogen, and the mixture was heated to reflux for 8 hours. After PH was adjusted to 1 with hydrochloric acid (50 ml), the mixture was filtered and extracted with benzene (3 × 90ml). The combined extracts were concentrated in vacuo to give brownish black oil.Fraction of reduced pressure distillation at 100 °C/67 Pa was collected to give gross product as a pale yellow solid. Recrystallization from mixture of dichloromethane and pentane (1/4, V/V) gave analytically pure product Tropolone(17.8 g,77%) as a white needle crystal, m.p. 50~51 °C.

Purification Methods

Crystallise tropolone from hexane or pet ether and sublime it at 40o/4mm. Also distil it at high vacuum. [Beilstein 8 IV 159.]