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Carbazole

From Wikipedia, the free encyclopedia
(Redirected from C12H9N)

Carbazole
Names
Preferred IUPAC name
9H-Carbazole[1]
Other names
9-azafluorene
dibenzopyrrole
diphenylenimine
diphenyleneimide
USAF EK-600
Identifiers
3D model (JSmol)
3956
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.542 Edit this at Wikidata
EC Number
  • 201-696-0
102490
KEGG
RTECS number
  • FE3150000
UNII
  • InChI=1S/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H checkY
    Key: UJOBWOGCFQCDNV-UHFFFAOYSA-N checkY
  • InChI=1/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
    Key: UJOBWOGCFQCDNV-UHFFFAOYAV
  • c1ccc2c(c1)c3ccccc3[nH]2
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 labelling:
GHS08: Health hazardGHS09: Environmental hazard
Warning
H341, H351, H400, H411, H413
P201, P202, P273, P281, P308+P313, 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).
checkY verify (what is checkYX markN ?)

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]

History

[edit]

Carl Graebe and Carl Glaser first isolated the compound from coal tar in 1872.[4]

Production

[edit]

Several routes exist beginning with extraction from coal tar by distillation. Carbazole concentrates in the anthracene distillate and is removed before anthraquinone production; that waste product is the major industrial carbazole source.[4][5] Polar compounds (e.g., ketones) selectively precipitate it from the anthracene; a more modern technique is simply selective crystallization from molten coal tar at high temperature[4] or low pressure (70 mmHg).[6]

Preparative methods:

Bucherer carbazole synthesis
Bucherer carbazole synthesis
  • A third method for the synthesis of carbazole is the Graebe–Ullmann reaction.
Graebe–Ullmann reaction
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.[9][10]

Fluorescence of (9H-carbazol-9-yl)(2,4-dichlorophenyl) methanone

Diphenylamine derivatives, being electron rich, are naturally oxidized to carbazoles when heated in air;[11] a similar reaction is the Mallory reaction.

Substituted carbazoles are most easily synthesized with transition metal coupling reactions. For applications that transition-metal impurities in the final product might inhibit, an alternative is nucleophilic aromatic substitution on dibenzothiophene dioxide.[12]

Natural Occurrence

[edit]

Carbazoles occur naturally in carbazole alkaloids. Carbazole alkaloids with unsubstituted benzene rings occur rarely. Olivacin has been found in the bark of Aspidosperma olivaceum and ellipticin in Ochrosia elliptica.[13] Some carbazole alkaloids, especially glybomin B, have been isolated from Glycosmis pentaphylla.[14][15]

Applications

[edit]

As carbazoles have a relatively rich UV-visible light spectrum, they see application as pigments[4] and photocatalysts.[16] The parent carbazole is used in Hydron Blue production[4] and aminoethylcarbazole is used in pigment violet 23 production.[17]

Pigment Violet 23 synthesis

Carbazoles stabilize triplet emitters in certain light-emitting diodes;[4] in general, they are electron photodonors (hole acceptors).[18]

Carbazole electrochemically oxidizes to a conductive polymer, which has not achieved substantial industrial use.[19] Polyvinylcarbazole is useful in the electrical and electronic industries, and certain carbazole novolaks are extremely heat resistant.[4]

In organic chemistry, carbazole proper is also an ingredient for several bioactive molecules. The insecticide Nirosan,[4] the cocaine overdose antidote Rimcazole, and the veterinary NSAID Carprofen are all made from carbazole. The topoisomerase II inhibitor ellipticine fuses carbazole to a pyridine ring.

See also

[edit]

References

[edit]
  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 212. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. 1 2 3 Lide DR (2007). CRC Handbook of Chemistry and Physics (88th ed.). CRC Press. pp. 3–86. ISBN 978-0-8493-0488-0.
  3. ↑ Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A (February 2011). "Hazardous compounds in tobacco smoke". International Journal of Environmental Research and Public Health. 8 (2): 613–628. doi:10.3390/ijerph8020613. PMC 3084482. PMID 21556207.
  4. 1 2 3 4 5 6 7 8 Collin G, Höke H, Talbiersky J. "Carbazole". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_059.pub2. ISBN 978-3-527-30673-2.
  5. ↑ Cofrancesco AJ, "Anthraquinone", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, p. 5, doi:10.1002/0471238961.0114200803150618.a01, ISBN 9780471238966
  6. ↑ Betts WD, "Tar and Pitch", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, p. 5, doi:10.1002/0471238961.20011802052020.a01, ISBN 9780471238966
  7. ↑ Rogers CU, Corson BB (1950). "1,2,3,4-Tetrahydrocarbazole (Carbazole, 1,2,3,4-tetrahydro-)". Organic Syntheses. 30: 90. doi:10.15227/orgsyn.030.0090; Collected Volumes, vol. 4, p. 884.
  8. ↑ Wang Z (2010). "Bucherer Carbazole Synthesis". Comprehensive Organic Name Reactions and Reagents. pp. 549–552. doi:10.1002/9780470638859.conrr120. ISBN 9780470638859.
  9. ↑ Graebe C, Ullman F (1896). "Ueber eine neue Carbazolsynthese". Justus Liebigs Ann. Chem. (in German). 291 (1): 16–17. doi:10.1002/jlac.18962910104.
  10. ↑ Bremer O (1934). "Über die Bedeutung der Graebe-Ullmannschen Carbazolsynthese und deren Übertragung auf N-substituierte Pyridino-triazole". Justus Liebigs Ann. Chem. (in German). 514 (1): 279–291. doi:10.1002/jlac.19345140116.
  11. ↑ Vogt PF, Gerulis JJ. "Amines, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Vol. 2. Weinheim: Wiley-VCH. p. 703. doi:10.1002/14356007.a02_037. ISBN 978-3-527-30673-2.
  12. ↑ Bhanuchandra M, Hideki Y. "Dibenzothiophene 5,5-dioxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn02046.
  13. ↑ Breitmaier E (1997), Alkaloide, Wiesbaden: Springer Fachmedien, p. 49, ISBN 978-3-519-03542-8
  14. ↑ Chen Y, Tang C, Wu Y, Mo S, Wang S, Yang G, et al. (June 2015). "Glycosmisines A and B: isolation of two new carbazole-indole-type dimeric alkaloids from Glycosmis pentaphylla and an evaluation of their antiproliferative activities". Organic & Biomolecular Chemistry. 13 (24): 6773–6781. doi:10.1039/c5ob00695c. PMID 26008648.
  15. ↑ Tan MA, Sharma N, An SS (March 2022). "Phyto-Carbazole Alkaloids from the Rutaceae Family as Potential Protective Agents against Neurodegenerative Diseases". Antioxidants. 11 (3). Basel, Switzerland: 493. doi:10.3390/antiox11030493. PMC 8944741. PMID 35326143.
  16. ↑ Rizzo CJ (2005). "N-Methylcarbazole". N -Methylcarbazole. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00578. ISBN 0-471-93623-5.
  17. ↑ US 4345074, Hufnagel T, Hetschko M, "Process for the manufacture of a violet organic pigment, C.I. Pigment Violet 23", issued 17 August 1982, assigned to Sanofi Aventis Deutschland GmbH
  18. ↑ Wang Y, "Photoconductive polymers", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, p. 15, doi:10.1002/0471238961.1608152023011407.a01, ISBN 9780471238966
  19. ↑ Naarmann H. "Polymers, Electrically conducting". Ullmann's Encyclopedia of Industrial Chemistry. Vol. 29. Weinheim: Wiley-VCH. p. 309. doi:10.1002/14356007.a21_429. ISBN 978-3-527-30673-2.
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