Carbazole | |
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9H-carbazole |
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Other names
9-azafluorene, dibenzopyrrole, diphenylenimine, diphenyleneimide, USAF EK-600 |
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Identifiers | |
CAS number | 86-74-8 |
PubChem | 6854 |
ChemSpider | 6593 |
UNII | 0P2197HHHN |
DrugBank | DB07301 |
KEGG | C08060 |
ChEBI | CHEBI:27543 |
ChEMBL | CHEMBL243580 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C12H9N |
Molar mass | 167.206 g mol−1[1] |
Density | 1.301g/cm^3 |
Melting point |
246.3 °C[1] |
Boiling point |
354.69 °C[1] |
Hazards | |
Flash point | 220 °C[1] |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene ring 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 4a–9a double bond in carbazole).
Contents |
A classic laboratory organic synthesis for carbazole is the Borsche–Drechsel cyclization.[2][3]
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–Ullmann reaction. 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]
2010 and 2011 have seen wide spread shortages of Carbazole.
Carbozole is used in the production of Pigment Violet 23.