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Usage

Uses

Used in Dye and Pigment Industry:
4-Aminocarbazole is used as a chemical intermediate for the synthesis of various dyes and pigments, particularly in the production of indigo dyes. Its unique structure contributes to the color and stability of these dyes, making it a valuable component in this industry.
Used in Pharmaceutical Industry:
4-Aminocarbazole is used as a building block in the synthesis of various drugs and pharmaceutical compounds. Its versatile chemical structure allows for the development of new and innovative medications, enhancing the range of treatments available for various health conditions.
Used in Anticancer Research:
4-Aminocarbazole is used as a subject of study in anticancer research for its potential to inhibit the growth of certain cancer cells. Its promising results in this area highlight its potential as a therapeutic agent in the fight against cancer.

InChI:InChI=1/C12H10N2/c13-9-5-3-7-11-12(9)8-4-1-2-6-10(8)14-11/h1-7,14H,13H2

Upstream product

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• 53290-48-5 2-amino-2'-phthalimidobiphenyl 

Relevant academic research and scientific papers

Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium

Primary anilines are essential building blocks to synthesize various pharmaceuticals, agrochemicals, pigments, electronic materials, and others. To date, the syntheses of primary anilines mostly rely on the reduction of nitroarenes or the transition-metal-catalyzed Ullmann, Buchwald-Hartwig and Chan-Lam cross-coupling reactions with ammonia, in which non-renewable petroleum-based chemicals are typically used as feedstocks via multiple step syntheses. A long-standing scientific challenge is to synthesize various primary anilines directly from renewable sources. Herein, we report a general method to directly convert a broad range of phenols into the corresponding primary anilines with the cheap and widely available hydrazine as both amine and hydride sources with simple Pd/C as the catalyst.

Synthesis of Carbazole, Acridine, Phenazine, 4H-Benzo[def]carbazole and Their Derivatives by Thermal Cyclization Reaction of Aromatic Amines

A variety of nitrogen-containing heterocycles were synthesized by passing vapors of aromatic amines over calcium oxide at 450-650 °C under nitrogen carrier gas. Reaction of 2-aminobiphenyl 3a at 560 °C gave carbazole 4 in 80% yield. Reaction of 2,2′-diaminobiphenyl 3b afforded a mixture of carbazole 4 and 4-aminocarbozole 6b. In the case of 2-amino-2′ -nitrobiphenyl 3c, benzo[c]cinnoline 7 was obtained along with carbazole 4. Reaction of 2-amino-2′-methoxybiphenyl 3d gave four products of carbazole 4, 4-hydroxycarbazole 6e, phenanthridine 8 and dibenzofuran 9. Reaction of 2-aminodiphenylmethane 5a afforded acridine 10. In the case of 2-aminobenzophenone 5b, acridone 11 was obtained as a major product. Reaction of 2-aminobenzhydrol 5c gave acridine 10. When 2-aminodiphenylamine 5d was reacted, phenazine 12 was obtained in good yield. In contrast, reaction of 2-aminodiphenyl ether 5e produced only 2-hydroxydiphenylamine 13. Reaction of 4-aminophenanthrene 14 produced 4H-benzo[def]carbazole 15 in 61% yield.

Photolysis of 2-Amino-2'-azidobiphenyls: Formal Formation of Internally Trapped Didehydroazepines

Photolysis of 2-amino-2'-azidobiphenyls in diethylamine gave 4,10-dihydroazepinoindoles (7), the structure of which corresponded to the didehydroazepines formally trapped with an internal amino group.However, the yields of 7 were considered low, which was due to the significant intramolecular interaction of the photolytically generated nitrene with an amino group, to afford benzocinnoline as a final product.