19402-87-0

Usage

Uses

Used in Electronics Industry:
9-Benzylcarbazole is used as a monomer in the synthesis of organic semiconductor materials for its desirable electronic properties. It is particularly utilized in the production of electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells, where its thermal stability and high electron mobility contribute to improved device performance.
Used in Medicinal Chemistry:
9-Benzylcarbazole has shown potential in the field of medicinal chemistry, with studies indicating its possible anti-cancer and anti-inflammatory properties. It is being explored as a candidate for the development of new therapeutic agents targeting various diseases and conditions.

InChI:InChI=1/C19H15N/c1-2-8-15(9-3-1)14-20-18-12-6-4-10-16(18)17-11-5-7-13-19(17)20/h1-13H,14H2

Upstream product

• 23560-25-0 carbazole nitranion 
• 100-44-7 benzyl chloride 
• 3459-92-5 DBC 
• 86-74-8 9H-carbazole 
• 621-84-1 O-benzyl carbamate 
• 17763-95-0 2,2'-bis-<<(trifluoromethyl)sulfonyl>oxy>biphenyl 
• 1073968-42-9 C₁₉H₁₆⁽²⁾HN 
• 52648-48-3 N-(phenylmethyl)-(1,1'-biphenyl)-2-amine 
• 19264-68-7 9-benzoyl-9H-carbazole 
• 189999-35-7 [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate 
• 100-46-9 benzylamine 
• 2113-51-1 2-iodobiphenyl 
• 606-87-1 N,N-diphenylbenzylamine 
• 124337-34-4 9-benzotriazole-1-ylmethyl-9H-carbazole 

Downstream Products

• 52915-10-3 1-(9-benzyl-carbazol-3-yl)-ethanone 
• 481695-75-4 1,1'-(9-benzyl-9H-carbazole-3,6-diyl)diethanone 
• 1592-95-6 3-bromo-9H-carbazole 
• 118599-27-2 9-benzyl-3,6-dibromo-9H-carbazole 
• 94127-10-3 9-benzyl-3-nitro-9H-carbazole 
• 19264-68-7 9-benzoyl-9H-carbazole 
• 1914-12-1 bis-(9H-carbazol-9-yl) 
• 86-74-8 9H-carbazole 
• 96853-15-5 9-benzyl-3,6-diiodo-9H-carbazole 
• 339576-55-5 3-bromo-9-benzyl-9H-carbazole 
• 229-87-8 phenanthridine 
• 85-01-8 phenanthrene 
• 51761-07-0 9H-carbazole-3-carbaldehyde 
• 259686-23-2 9-benzyl-3,6-di-tert-octylcarbazole 

Relevant academic research and scientific papers

Accelerative effects of carbazole-type alkaloids from Murraya koenigii on neurite outgrowth and their derivative’s in vivo study for spatial memory

Murraya koenigii is a medicinal plant that contains several carbazole-type alkaloids as its characteristic constituents. Blood–brain barrier permeable constituents of M. koenigii accelerated neurite outgrowth in PC-12 cells. Nine compounds were isolated f

New carbazole alkaloids from Murraya euchrestifolia

Two new monomeric and one dimeric carbazole alkaloids were isolated from root bark of Murraya euchrestifolia HAYATA collected in Taiwan. Their structures were elucidated by spectrometric and synthetic studies. The structures of the monomeric carbazoles were assigned as 3-formyl-7-hydroxy-9H-carbazole (1) and N-methoxy-3-hydroxymethyl 9H-carbazole (2). The dimeric carbazole, named chrestifoline-D (9), was found to be identical with the oxidation product of bismurrayafoline-A (10).

Thermally activated delayed fluorescence in 1,3,4-oxadiazoles with π-extended donors

Here, we describe the synthesis of five 1,3,4-oxadiazole-based donor-acceptor materials, using dendritic carbazole-based donors 9′H-9,3′:6′9″-tercarbazole (terCBz) and N3,N3,N6,N6-tetra-p-tolyl-9H-carbazole-3,6-diamine (TTAC). Due to the strongly donating and highly twisted nature of the TTAC donor as well as the spatially separated hole-particle wavefunctions, three of the five compounds exhibited thermally activated delayed fluorescence (TADF) in spite of a relatively large ΔEST measured through phosphorimetry (0.33-0.37 eV). These materials demonstrated photoluminescence quantum yields as high as 0.89 in toluene, with emission maxima ranging from 474 to 495 nm in the solid state. Additionally, two materials containing only terCBZ donor(s) exhibited deep blue fluorescence, with Commission Internationale de l'éclairage coordinates of (0.16, 0.05); the weaker nature of the terCBz donor results in a prohibitively large ΔEST (0.68-0.77 eV). A gap-tuned range-separated hybrid functional (ωB97XD*) was used to rigorously calculate triplet energies, while a systematic analysis of electronic structures and photophysical properties provided further insight into the properties of these materials. These findings ultimately contribute a synthetically facile approach toward highly emissive TADF emitters using a 1,3,4-oxadiazole motif.

THE APPLICATION OF ULTRASOUND TO THE N-ALKYLATION OF AMINES USING PHASE TRANSFER CATALYSIS

The application of ultrasound to the N-alkylation of a variety of amines by alkyl halides under phase transfer conditions (polyethylene glycol methyl ether and alkylammonium compounds as catalysts) leads to a decrease in the time required to effect reaction.

Atom Transfer Radical Polymerization-Inspired Room Temperature (sp3)C-N Coupling

A simple nonphotochemical procedure is reported for Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and amides. The process is loosely based on the Goldberg reaction but takes place readily at room temperature. It uses Cu(I)Br, a commonly used and inexpensive atom transfer radical polymerization precatalyst, along with the cheap ligand N,N,N′,N″,N″-pentamethyldiethylenetriamine, to activate the R-X bond of the substrate via inner-sphere electron transfer. The procedure brings about productive C-N bond formation between a range of alkyl halide substrates with heterocyclic aromatic amines and amides. The mechanism of the coupling step, which was elucidated through application of computational methods, proceeds via a unique Cu(I) → Cu(II) → Cu(III) → Cu(I) catalytic cycle, involving (a) inner-sphere electron transfer from Cu(I) to the alkyl halide to generate the alkyl radical; (b) successive coordination of the N-nucleophile and the radical to Cu(II); and finally reductive elimination. In the absence of a nucleophile, debrominative homocoupling of the alkyl halide occurs. Control experiments rule out SN-type mechanisms for C-N bond formation.

Organic fluorescent dendrimer thin film material and preparation method thereof

The invention discloses an organic fluorescent dendritic molecular film material and a preparation method thereof, and relates to the technical field of fluorescence sensing. A dendritic molecular main chain skeleton is formed by a central core unit A and

Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents

Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards different bacterial strains (including one multidrug-resistant clinical isolate) and one fungal strain with minimum inhibitory concentrations (MICs) between 0.5 and 16 μg/ml. Compounds 8f and 9d showed the most potent inhibitory activities (MICs of 0.5–2 μg/ml). Furthermore, compounds 8b, 8d, 8f, 8k, 9b and 9e with antimicrobial activities were not cytotoxic to human gastric cancer cell lines (SGC-7901 and AGS) or a normal human liver cell line (L-02). Structure–activity relationship analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency and reducing the toxicity of the carbazole compounds. In vitro enzyme activity assays suggested that compound 8f binding to dihydrofolate reductase might account for the antimicrobial effect.

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.

Method for synthesizing carbazole derivative

The invention aims to provide a method for synthesizing a carbazole derivative. The method is characterized in that palladium chloride is used as a catalyst, 2, 2' - dibromobiphenyl is used as an electrophilic reagent, primary amine is taken as a nucleophile, and the carbazole derivative is directly cross-coupled under the conditions of toluene as a solvent and an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N -Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C-N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.