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Carbazole
Carbazole.png
Carbazole-3D-vdW.png
IUPAC name
Other names 9-azafluorene, dibenzopyrrole, diphenylenimine, diphenyleneimide, USAF EK-600
Identifiers
CAS number 86-74-8 Yes check.svgY
PubChem 6854
SMILES
InChI
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]
 Yes check.svgY (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

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]

Safety

Safety information for carbazole is available here.

Related aromatic compounds

References

  1. ^ a b c d Lide, David R. (2007). CRC Handbook of Chemistry and Physics, 88th Edition. CRC Press. pp. 3–86. ISBN 978-0849304880.  
  2. ^ W. Borsche (1908). "Ueber Tetra- und Hexahydrocarbazolverbindungen und eine neue Carbazolsynthese. (Mitbearbeitet von. A. Witte und W. Bothe.)". Justus Liebig's Annalen der Chemie 359 (1-2): 49–80. doi:10.1002/jlac.19083590103.  
  3. ^ E. Drechsel (1888). "Ueber Elektrolyse des Phenols mit Wechselströmen". Journal für praktische Chemie 38 (1): 65–74. doi:10.1002/prac.18880380105.  
  4. ^ Organic Syntheses, Coll. Vol. 4, p.884 (1963); Vol. 30, p.90 (1950). Link
  5. ^ Graebe-Ullmann reaction
  6. ^ Carl Graebe and Fritz Ullmann (1896). "Ueber eine neue Carbazolsynthese". Justus Liebig's Annalen der Chemie 291 (1): 16–17. doi:10.1002/jlac.18962910104.  
  7. ^ O. Bremer (1934). "Über die Bedeutung der Graebe-Ullmannschen Carbazolsynthese und deren Übertragung auf N-substituierte Pyridino-triazole". Justus Liebigs Annalen der Chemie 514: 279–291. doi:10.1002/jlac.19345140116.  
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