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Usage

Uses

Used in Pharmaceutical Industry:
9H-Carbazole, 9-chlorois used as a starting material for the synthesis of various pharmaceutical compounds due to its unique chemical structure and reactivity. The 9-chloro substitution on the carbazole ring allows for further functionalization and modification, enabling the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
9H-Carbazole, 9-chlorois utilized as a precursor in the production of dyes, particularly those with specific color properties and stability. The presence of the chloro group on the carbazole ring contributes to the dye's characteristics, making it suitable for various applications, such as textiles, plastics, and printing inks.
Used in Polymer Industry:
9H-Carbazole, 9-chloroserves as a key building block in the synthesis of polymers with specific properties, such as electrical conductivity, thermal stability, and mechanical strength. The chloro substitution on the carbazole ring allows for the creation of polymers with tailored characteristics, making them suitable for use in various industries, including electronics, automotive, and aerospace.

Upstream product

• 86-74-8 9H-carbazole 

Downstream Products

• 64389-47-5 1,6-dichlorocarbazole 
• 5599-70-2 1-chlorocarbazole 
• 5599-71-3 3,6-dichloro-9H-carbazole 
• 86-74-8 9H-carbazole 
• 2732-25-4 3-chloro-9H-carbazole 

Relevant academic research and scientific papers

On the Synthesis and Isolation of Chlorocarbazoles Obtained by Chlorination of Carbazoles

Carbazole (1) undergoes electrophilic aromatic substitution with various chlorinating reagents. Although 3-chlorocarbazole (1b), 3,6-dichlorocarbazole (1d) and 1,3,6,8-tetrachlorocarbazole (1f) obtained by chlorination of carbazole were isolated and characterized sometime ago, 1-chlorocarbazole (1a), 1,6-dichlorocarbazole (1c) and 1,3,6-trichlorocarbazole (1e) had never been isolated from the reaction mixtures. The preparation and subsequent isolation and characterization of 1a, 1b, 1e, 1d, 1e and 1f are reported (mp, tF, Rf, 1H- and 13C-nmr, ms). Physical and spectroscopic properties of le are compared with those of 1b and 1d in order to show that the former is the major product obtained in several chlorinating processes. As chlorinating reagents, chlorine in glacial acetic acid, sulfuryl chloride, N-chlorosuccinimide, N-chlorosuccinimide-silica gel, N-chlorobenzotriazole, and N-chlorobenzotriazole-silica gel in dichloromethane and in chloroform have been used and their uses have been compared. The chlorination reaction of different carbazole derivatives such as 2-hydroxycarbazole (2), 2-acetoxycarbazole (3), 3-bromocarbazole (4) and 3-nitrocarbazole (5) was also studied and the corresponding chloro derivatives 2a, 2b, 2c, 2d, 3a, 3b, 3c, 3d, 3e, 3f, 4a, 4b, 4c, 4d, 5a and 5b are described for the first time. Semiempirical PM3 calculations have been performed in order to predict reactivity of carbazole (1), substituted carbazoles 2-5 and chlorocarbazoles (Scheme 1). Theoretical and experimental results are discussed briefly.

Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole

The chlorination of carbazole with sodium hypochlorite in CH2Cl2, CHCl3, or CCl4 gave N-chlorocarbazole in 63-95percent yield.It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole.These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction.In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed.No evidence for an intramolecular rearrangement was found.