Samiksha Jaiswal (Editor)

Carbazole

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Formula  C12H9N
Melting point  246.3 °C
Density  1.3 g/cm³
Molar mass  167.206 g/mol
Boiling point  354.7 °C

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 2–3 position of indole (equivalent to the 9a–4a double bond in carbazole, respectively).

Contents

Carbazole wwwsigmaaldrichcomcontentdamsigmaaldrichstr

Synthesis

A classic laboratory organic synthesis for carbazole is the Borsche–Drechsel cyclization.

Carbazole Carbazole Wikipedia

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. 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–Ullmann reaction.

Carbazole 27Dibromocarbazole 27Dibromo9Hcarbazole 136630392 Ossila

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.

Use

Aminoethylcarbazole is used in the production of pigment violet 23.

  • Rimcazole is also made from carbazole proper.
  • Related aromatic compounds

  • Indoline
  • Indole
  • Carboline
  • Fluorene
  • Pyrrole
  • N-Vinylcarbazole

  • Carbazole Carbazole C12H9N ChemSpider
    Carbazole Carbazole Wikipedia
    Carbazole 9Methyl9Hcarbazole2carbaldehyde AldrichCPR SigmaAldrich

    References

    Carbazole Wikipedia


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