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Thallium(III) nitrate

Chemical compound From Wikipedia, the free encyclopedia

Thallium(III) nitrate
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Thallium(III) nitrate, also known as thallic nitrate, is a thallium compound with chemical formula Tl(NO3)3.[1] Normally found as the trihydrate, it is a colorless and highly toxic salt which hydrolyses in water to thallium(III) oxide.[2] It is a strong oxidizing agent useful in organic synthesis.

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Preparation

The trihydrate is prepared by dissolving thallium(III) oxide in concentrated nitric acid at 80 °C, followed by cooling of the resulting solution:[3]

Tl2O3 + 6 HNO3 → 2 Tl(NO3)3 + 3 H2O

Structure

Thallium(III) nitrate trihydrate, Tl(NO3)3·3H2O, crystallizes in the hexagonal crystal system and consists of a nine-coordinate thallium center with three bidentate nitrate ligands and three monodentate water ligands.[4]

Organic synthesis

Despite its toxicity, thallium(III) nitrate is sometimes used in the laboratory, such as in the oxidation of methoxyl phenols to quinone acetals:[5]

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Another use of thallium(III) nitrate is the oxidization of alkenes to acetals, cyclic alkenes to ring contracted aldehydes, and terminal alkynes to carboxylic acids. Ketones are also oxidized to carboxylic acids or esters in the presence of methanol. Illustrated below is an example of alkene oxidation to an acetal:[5][6]

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References

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