Tropolone

Tropolone is an organic compound with the chemical formula C7H6O2. It is a seven-membered aromatic ring and is notable for its uncommon 7-membered ring structure. Tropolone was first isolated in 1935 by the German chemist Walter Reppe and his colleagues, who produced it from cresol and carbon monoxide in a process now known as Reppe chemistry.

Structure and properties[edit | edit source]

Tropolone consists of a seven-membered ring with alternating single and double bonds, similar to the structure of benzene. However, unlike benzene, tropolone has a ketone functional group at one of its positions. This ketone group is in a state of continuous tautomerism with a nearby hydroxyl group, resulting in a structure that is best represented as a resonance hybrid of two forms.

Tropolone is a pale yellow solid that is soluble in water, alcohol, and ether. It has a characteristic strong odor and a bitter taste.

Synthesis[edit | edit source]

Tropolone can be synthesized from cresol and carbon monoxide in a process known as Reppe chemistry. This process involves the carbonylation of cresol to give a lactone, which is then rearranged to give tropolone.

Uses[edit | edit source]

Tropolone is used as a chelating agent in the synthesis of metal complexes. It is also used as a ligand in organometallic chemistry. In addition, tropolone has been studied for its potential use in organic electronics due to its ability to accept and donate electrons.

Safety[edit | edit source]

Tropolone is considered to be a mild irritant. It can cause irritation to the skin, eyes, and respiratory tract if inhaled or contacted.

References[edit | edit source]

Tropolone Resources
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