What Is Carbazole?
Carbazole, a heterocyclic compound with the chemical formula C12H9N, also known as dibenzopyrrole, was discovered in coal tar in 1872 and is present in crude oil. It is purified from anthracene oil, a fraction of coal tar.
Uses of Carbazole
Carbazole has diverse uses including in dyes, synthetic raw materials for plastics, photographic dry plates, and organic electroluminescence. Its derivatives with photoconductive properties are used in photoconductor drums for copiers. Carbazole alkaloids are known for antibacterial, antioxidant, and antitumor effects, with derivatives like Carvedilol and Carprofen used in pharmaceuticals.
Properties of Carbazole
Carbazole has a melting point of 246.3°C, a boiling point of 354.69°C, and a flash point of 220°C. Its nitrogen atom releases electrons, giving the molecule an electric dipole when an electron-withdrawing group is introduced.
Structure of Carbazole
Carbazole, a colorless crystal with a molecular weight of 167.206, is soluble in acetone but insoluble in water. The introduction of an electron-withdrawing group gives the molecule an electric dipole.
Other Information on Carbazole
1. Classical Synthesis of Carbazole
Bucherer carbazole synthesis, a classical method, involves reacting arylhydrazine and naphthol with sodium hydrogen sulfite. The Borsche-Drechsel cyclization and the Graebe-Ullmann reaction are other synthesis methods in the laboratory.
2. Related Compounds of Carbazole
Related compounds include pyrrole and indole, with pyrrole being an amine of a heterocyclic aromatic compound and indole having a fused structure of a pyrrole ring and a benzene ring.