69386-36-3

Usage

Uses

Used in Organic Electronics Industry:
2-TERT-BUTYL-9H-CARBAZOLE is used as a material in the manufacturing of organic light-emitting diodes (OLEDs) for its ability to contribute to the development of efficient and stable OLEDs.
Used in Semiconductor Material Industry:
2-TERT-BUTYL-9H-CARBAZOLE is used as a potential semiconductor material due to its unique properties that make it suitable for applications in the field of organic electronics.
Used in Photovoltaic Devices:
2-TERT-BUTYL-9H-CARBAZOLE is used as a photoactive material in photovoltaic devices, leveraging its good charge transport properties for improved performance in solar energy conversion.
Overall, 2-TERT-BUTYL-9H-CARBAZOLE has garnered interest in the realm of material science for its potential use in advanced electronic and optoelectronic technologies, making it a valuable compound for future innovations in these industries.

InChI:InChI=1/C16H17N/c1-16(2,3)11-8-9-13-12-6-4-5-7-14(12)17-15(13)10-11/h4-10,17H,1-3H3

Upstream product

• 70728-97-1 4,4′-di-tert-butyl-[1,1′-biphenyl]-2,2′-diamine 
• 577-19-5 2-nitrophenyl bromide 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 1140969-82-9 C₁₆H₁₇N₃ 
• 93026-60-9 (3-tert-butyl-phenyl)-phenyl-amine 
• 1429337-45-0 4'-(tert-butyl)-2-iodo-1,1'-biphenyl 
• 1600505-68-7 3-(2-methylpropan-1-ylium-2-yl)dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate 
• 744262-30-4 4'-(t-butyl)-[1,1‘-biphenyl]-2-amine 
• 615-43-0 2-iodophenylamine 

Relevant academic research and scientific papers

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes

A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.

Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole

A nitrogen-iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a nonsteroidal anti-inflammatory drug) were efficiently established through this protocol.

Carbazole compound, and synthesis method and application of compound

The invention discloses a carbazole compound represented by a formula (2) and a synthesis method of the compound. A high-iodine salt is taken as a reaction raw material, and under the action of an inorganic nitrogen reagent, an additive, a base and a metal catalyst, a reaction is carried out in a solvent under a condition of 80-150 DEG C to obtain various carbazole compounds. According to the method provided by the invention, nitrogen atoms are introduced in a later period, so that the non-compatibility of nitrogen heterocyclic rings to the reaction conditions such as the metal catalyst and the like in an early reaction period is avoided. In addition, two aryl groups in the high-iodine salt are fully utilized, so that the atomic economic efficiency of the method provided by the present invention is fully exhibited. The carbazole compound prepared by the method provided by the invention can be further applied to the synthesis of non-steroidal anti-inflammatory drug carprofen.

One-pot synthesis of carbazoles via tandem C-C cross-coupling and reductive amination

We have developed a highly efficient synthetic route to carbazoles that employs sequential C-C/C-N bond formation via Suzuki cross-coupling and Cadogan cyclization using commercially available or easily preparable starting materials. The developed method is compatible with electron neutral, rich or deficient substrates. The synthetic utility of this method was demonstrated by the concise syntheses of four natural products (glycozoline, glycozolicine, glycozolidine and clausenalene).

Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds

We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations. Controlled fusion: A transition-metal-free, low-temperature, and regioselective intramolecular amination of aromatic C(sp2)-H bonds provides fused N-heterocycles. This reaction is operationally simple and scalable (1-10 mmol) and the scope of substrates is wide (see scheme). Density functional calculations indicate that a stepwise electrophilic aromatic cyclization mechanism may be operative.

Recyclable copper catalyzed nitrogenation of biphenyl halides: A direct approach to carbazoles

A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C-H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle.

Kinesin spindle protein (KSP) inhibitors with 2,3-fused indole scaffolds

Mitotic kinesin spindle protein (KSP) is involved in the assembly of the bipolar spindle during cell division. On the basis of a common 2,3-fused indole substructure within the complex frameworks of terpendole E and other KSP inhibitors, the carbazoles with a bulky alkyl group were identified as a novel KSP inhibitory scaffold. Additionally, among several naturally occurring cell growth inhibitors with 2,3-fused indole structures,β-carboline alkaloids, harman and harmine, showed moderate inhibition of KSP.

Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: Synthesis and mechanistic study

(Chemical Equation Presented) An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.

Rh2(II)-catalyzed synthesis of carbazoles from biaryl azides

An array of carbazoles (23 examples) can be synthesized from substituted biaryl azides at 60 °C using substoichio-metric quantities of Rh 2(O2CC3F7)4 or Rh 2(O2CC7H15)4.