Carbazole
IUPAC name	9H-carbazole
Other names	9-azafluorene, dibenzopyrrole, diphenylenimine, diphenyleneimide, USAF EK-600
Identifiers
CAS number	86-74-8 Y
PubChem	6854
SMILES	c1cccc3c1c2c(cccc2)n3
InChI	1/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
InChI key	UJOBWOGCFQCDNV-UHFFFAOYAV
ChemSpider ID	6593
Properties
Molecular formula	C12H9N
Molar mass	167.206 g mol−1[1]
Melting point	246.3 °C[1]
Boiling point	354.69 °C[1]
Hazards
Flash point	220 °C[1]
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 1 Synthesis 2 Safety 3 Related aromatic compounds 4 References

[edit] Synthesis

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 a first step a N-phenyl-1,2-diaminobenzene (N-phenyl-o-phenylenediamine) is converted into a diazoniumsalt 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]

[edit] Safety

Safety information for carbazole is available here.

[edit] Related aromatic compounds

• Indoline
• Indole
• Carboline
• Fluorene
• Pyrrole

[edit] References