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  • Product overview锛Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole structure but in which a second benzene ring is fused onto the five-membered ring at the 2鈥3 position of indole (equivalent to the 9a鈥4a double bond in carbazole respectively).

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A classic laboratory organic synthesis for carbazole is the Borsche鈥揇rechsel cyclization.[2][3]

  • Borsche鈥揇rechsel synthesis

In the first step phenylhydrazine is condensed with cyclohexanone to the corresponding imine. The second step is a hydrochloric acid catalyzed rearrangement reaction and ring-closing reaction to tetrahydrocarbazole. In one modification, both steps are rolled into one by carrying out the reaction in acetic acid.[4] In the third step this compound is oxidized by Red lead to carbazole itself. Another classic is the Bucherer carbazole synthesis

A second method for the synthesis of carbazole is the Graebe鈥揢llmann reaction.

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In the first step, an N-phenyl-1,2-diaminobenzene (N-phenyl-o-phenylenediamine) is converted into a diazonium salt which instantaneously forms a 1,2,3-triazole. The triazole is unstable and at elevated temperatures nitrogen is set free and the carbazole is formed.[5][6][7]

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