Carbazol

Carbazol
Identificare
SMILES
Număr CAS86-74-8
ChEMBLCHEMBL243580
PubChem CID6854
Formulă chimicăC₁₂H₉N[1]  Modificați la Wikidata
Masă molară167,073 u.a.m.[1]  Modificați la Wikidata
Punct de topire243 °C[2]  Modificați la Wikidata
Punct de fierbere354,7 °C[3]  Modificați la Wikidata la 101,325 kPa
Sunt folosite unitățile SI și condițiile de temperatură și presiune normale dacă nu s-a specificat altfel.
Modifică date / text Consultați documentația formatului

Carbazolul este un compus heterociclic aromatic cu structură triciclică, format din două nuclee benzenice (din șase atomi fiecare), legate între ele printr-un nucleu heterociclic cu azot. Structura chimică a compusului se bazează pe cea a indolului. Este un constituent al fumului de țigară.[4]

Obținere

În laborator

O metodă clasică de obținere în laborator a carbazolului este ciclizarea Borsche–Drechsel.[5][6]

Sinteza Borsche–Drechsel

Într-o primă etapă, fenilhidrazina este condensată cu ciclohexanona cu obținerea iminei corespunzătoare. A doua etapă presupune o reacție de rearanjare catalizară cu acid clorhidric și ulterior o reacție de închidere a nucleului cu obținerea de tetrahidrocarbazol.[7] În cea de-a treia etapă, acest compus este oxidat în prezența tetroxidului de plumb la carbazol.

Proprietăți

Vezi și

Referințe

  1. ^ a b c „Carbazol”, CARBAZOLE (în engleză), PubChem, accesat în  
  2. ^ Jean-Claude Bradley Open Melting Point Dataset 
  3. ^ Basic laboratory and industrial chemicals: A CRC quick reference handbook[*][[Basic laboratory and industrial chemicals: A CRC quick reference handbook (book by David Lide from 1993)|​]]  Verificați valoarea |titlelink= (ajutor)
  4. ^ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (). „Hazardous Compounds in Tobacco Smoke”. Int. J. Environ. Res. Publ. Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. PMC 3084482 Accesibil gratuit. PMID 21556207. 
  5. ^ W. Borsche (). „Ueber Tetra- und Hexahydrocarbazolverbindungen und eine neue Carbazolsynthese. (Mitbearbeitet von. A. Witte und W. Bothe.)”. Justus Liebigs Ann. Chem. (în German). 359 (1–2): 49–80. doi:10.1002/jlac.19083590103. 
  6. ^ E. Drechsel (). „Ueber Elektrolyse des Phenols mit Wechselströmen”. J. prakt. Chem. (în germană). 38 (1): 65–74. doi:10.1002/prac.18880380105. 
  7. ^ Rogers, Crosby U.; Corson, B. B. (), „1,2,3,4-Tetrahydrocarbazole (Carbazole, 1,2,3,4-tetrahydro-)”, Org. Synth., 30: 90, doi:10.15227/orgsyn.030.0090 ; Collective Volume, 4, p. 884 

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