Chemistry:Carbazole
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| Names | |
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| Preferred IUPAC name
9H-Carbazole[1] | |
| Other names
9-azafluorene
dibenzopyrrole diphenylenimine diphenyleneimide USAF EK-600 | |
| Identifiers | |
3D model (JSmol)
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| 3956 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| EC Number |
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| 102490 | |
| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
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| Properties | |
| C12H9N | |
| Molar mass | 167.211 g·mol−1 |
| Density | 1.301 g cm−3 |
| Melting point | 246.3 °C (475.3 °F; 519.5 K)[2] |
| Boiling point | 354.69 °C (670.44 °F; 627.84 K)[2] |
| −117.4 × 10−6 cm3 mol−1 | |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Warning |
| H341, H351, H400, H411, H413 | |
| P201, P202, P273, P281, P308+313, P391, P405, P501 | |
| Flash point | 220 °C (428 °F; 493 K)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
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).
Carbazole is a constituent of tobacco smoke.[3]
Synthesis
A classic laboratory organic synthesis for carbazole is the Borsche–Drechsel cyclization.[4][5]
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.[6] In the third step, this compound is oxidized by red lead to carbazole itself.
Another classic is the Bucherer carbazole synthesis, which uses a naphthol and an aryl hydrazine.[7]
A third 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 released and the carbazole is formed.[8][9]
Applications
Aminoethylcarbazole is used in the production of pigment violet 23.
Related aromatic compounds
- Indoline
- Indole
- Carboline
- Fluorene
- Pyrrole
- N-Vinylcarbazole
References
- ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 212. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ↑ 2.0 2.1 2.2 Lide, David R. (2007). CRC Handbook of Chemistry and Physics, 88th Edition. CRC Press. pp. 3–86. ISBN 978-0-8493-0488-0.
- ↑ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". Int. J. Environ. Res. Public Health 8 (12): 613–628. doi:10.3390/ijerph8020613. PMID 21556207.
- ↑ W. Borsche (1908). "Ueber Tetra- und Hexahydrocarbazolverbindungen und eine neue Carbazolsynthese. (Mitbearbeitet von. A. Witte und W. Bothe.)" (in German). Justus Liebigs Ann. Chem. 359 (1–2): 49–80. doi:10.1002/jlac.19083590103. https://zenodo.org/record/1427575.
- ↑ E. Drechsel (1888). "Ueber Elektrolyse des Phenols mit Wechselströmen" (in de). J. Prakt. Chem. 38 (1): 65–74. doi:10.1002/prac.18880380105. https://zenodo.org/record/1427938.
- ↑ Rogers, Crosby U.; Corson, B. B. (1950). "1,2,3,4-Tetrahydrocarbazole (Carbazole, 1,2,3,4-tetrahydro-)". Organic Syntheses 30: 90. doi:10.15227/orgsyn.030.0090. http://www.orgsyn.org/demo.aspx?prep=CV4P0884.; Collective Volume, 4, pp. 884
- ↑ Wang, Zerong (2010). "Bucherer Carbazole Synthesis". Comprehensive Organic Name Reactions and Reagents. doi:10.1002/9780470638859.conrr120. ISBN 9780470638859.
- ↑ Carl Graebe; Fritz Ullmann (1896). "Ueber eine neue Carbazolsynthese" (in German). Justus Liebigs Ann. Chem. 291 (1): 16–17. https://zenodo.org/record/1427487.
- ↑ O. Bremer (1934). "Über die Bedeutung der Graebe-Ullmannschen Carbazolsynthese und deren Übertragung auf N-substituierte Pyridino-triazole" (in German). Justus Liebigs Ann. Chem. 514 (1): 279–291. doi:10.1002/jlac.19345140116.
External links
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Wikisource has the text of the 1911 Encyclopædia Britannica article Carbazol. |
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