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Carbazole

Base Information Edit
  • Chemical Name:Carbazole
  • CAS No.:86-74-8
  • Molecular Formula:C12H9N
  • Molecular Weight:167.21
  • Hs Code.:2933.90
  • European Community (EC) Number:201-696-0
  • NSC Number:3498
  • UNII:0P2197HHHN
  • DSSTox Substance ID:DTXSID4020248
  • Nikkaji Number:J3.896B
  • Wikipedia:Carbazole
  • Wikidata:Q424003
  • Metabolomics Workbench ID:51366
  • ChEMBL ID:CHEMBL243580
  • Mol file:86-74-8.mol
Carbazole

Synonyms:9-azafluorene;9H-carbazole;carbazole;dibenzo(b,d)pyrrole;dibenzopyrrole;diphenylenimine

Suppliers and Price of Carbazole
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • 9H-Carbazole
  • 1 g
  • $ 65.00
  • TRC
  • 9H-Carbazole
  • 50 g
  • $ 155.00
  • TCI Chemical
  • Carbazole >97.0%(GC)
  • 500g
  • $ 240.00
  • TCI Chemical
  • Carbazole >97.0%(GC)
  • 100g
  • $ 74.00
  • TCI Chemical
  • Carbazole >97.0%(GC)
  • 25g
  • $ 26.00
  • SynQuest Laboratories
  • 9H-Carbazole 98%
  • 25 g
  • $ 26.00
  • Sigma-Aldrich
  • Carbazole Carbazole for synthesis. CAS 86-74-8, molar mass 167.2 g/mol., for synthesis
  • 8202550250
  • $ 63.20
  • Sigma-Aldrich
  • Carbazole for synthesis
  • 250 g
  • $ 60.49
  • Sigma-Aldrich
  • Carbazole VETRANAL?, analytical standard
  • 250 mg
  • $ 49.50
  • Sigma-Aldrich
  • Carbazole VETRANAL
  • 250mg-r
  • $ 48.00
Total 39 raw suppliers
Chemical Property of Carbazole Edit
Chemical Property:
  • Appearance/Colour:white crystals or light brown powder 
  • Vapor Pressure:400 mm Hg ( 323 °C) 
  • Melting Point:243-246 °C(lit.) 
  • Refractive Index:1.767 
  • Boiling Point:355 °C at 760 mmHg 
  • PKA:17.00±0.30(Predicted) 
  • Flash Point:159.956 °C 
  • PSA:15.79000 
  • Density:1.23 g/cm3 
  • LogP:3.32110 
  • Storage Temp.:2-8°C 
  • Solubility.:acetone: soluble50mg/mL 
  • Water Solubility.:<0.1 g/100 mL at 19℃ 
  • XLogP3:3.7
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:0
  • Rotatable Bond Count:0
  • Exact Mass:167.073499291
  • Heavy Atom Count:13
  • Complexity:170
Purity/Quality:

99% *data from raw suppliers

9H-Carbazole *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn, DangerousN, Toxic
  • Hazard Codes:Xn,N,T 
  • Statements: 22-36/37/38-40-50/53-63-43-23/24/25-45-67-68-51/53 
  • Safety Statements: 26-36-60-61-36/37-24/25-23-53-45-36/37/39 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Nitrogen Compounds -> Amines, Polyaromatic
  • Canonical SMILES:C1=CC=C2C(=C1)C3=CC=CC=C3N2
  • Uses Important dye intermediate. Used in making photographic plates sensitive to ultraviolet light. Reagent for lignin, carbohydrates, and formaldehyde. Carbazole and its derivatives are widely used as an intermediate in synthesis of pharmaceuticals, agrochemicals, dyes, pigments and other organic compounds.?carbazole is also used in luminescence chemistry as a photosensitizing and additional charge transport material. Carbazole structure is a motif in pharmaceuticals such as carvedilol used to treat high blood pressure and to prevent cardiac arrhythmias and angina. Intermediate in production of dyes and UVsensitive photographic plates.
Technology Process of Carbazole

There total 581 articles about Carbazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With sulfuric acid; In 1,4-dioxane; at 18 ℃;
DOI:10.1023/A:1012341921034
Guidance literature:
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 80 ℃; for 101h;
DOI:10.3987/COM-97-7990
Refernces Edit

Organic dyes incorporating a thiophene or furan moiety for efficient dye-sensitized solar cells

10.1016/j.dyepig.2013.12.025

In this research, the main focus was on the development and characterization of four novel carbazole-based organic dyes for use in dye-sensitized solar cells (DSSCs). The dyes, containing either a furan or thiophene moiety, were designed with the aim of improving the photovoltaic performance of DSSCs. The synthesis involved the use of reactants such as 3,6-diiodo-9H-carbazole, various alkyl halides, and boronic acids, and included Suzuki cross-coupling and Knoevenagel condensation reactions to attach the donor, linker, and acceptor groups to the carbazole core. The characterization of these dyes was performed using NMR and mass spectrometry to confirm their structures, UV-Vis absorption spectroscopy to determine their absorption properties, and cyclic voltammetry to evaluate their electrochemical behavior. The photovoltaic performance of the DSSCs sensitized by these dyes was assessed through measurements of short-circuit current density (Jsc), open-circuit voltage (Voc), fill factor (FF), and overall conversion efficiency (η) under standard AM 1.5 solar light conditions, with comparisons made to a ruthenium complex dye N719.

Potent human dihydroorotate dehydrogenase inhibitory activity of new quinoline-4-carboxylic acids derived from phenolic aldehydes: Synthesis, cytotoxicity, lipophilicity and molecular docking studies

10.1016/j.bioorg.2020.104373

The study focuses on the synthesis and evaluation of a series of novel 2-substituted quinoline-4-carboxylic acids derived from phenolic aldehydes, which were designed to target human dihydroorotate dehydrogenase (hDHODH), an enzyme crucial for cancer cell proliferation. These compounds were tested for their inhibitory activity against hDHODH, cytotoxicity against cancer cell lines (MCF-7, A549, A375), and a normal cell line (HaCaT), as well as their lipophilicity. The purpose of these chemicals was to serve as potential chemotherapeutic agents, with the aim of developing new drugs that can inhibit hDHODH, thereby disrupting pyrimidine biosynthesis and hindering cancer cell growth. The study also included molecular docking studies to understand the structural differences that contribute to the varying levels of activity among the synthesized compounds.

Zigzag molecules from pyrene-modified carbazole oligomers: Synthesis, characterization, and application in OLEDs

10.1021/jo702075r

The research focuses on the synthesis, characterization, and application of pyrene-modified carbazole oligomers in organic light-emitting diodes (OLEDs). The purpose of the study was to create a series of monodisperse, ethynylene-linked oligocarbazoles with zigzag molecular backbones, which were designed to have stable, size-independent absorption and emission properties. The researchers aimed to investigate the impact of pyrene incorporation at different positions within the oligocarbazole main chain on the absorption and emission spectra, as well as to evaluate the optoelectronic performance of these materials in OLEDs. The conclusions drawn from the study indicated that the introduction of pyrene units effectively tuned the emission wavelengths and significantly improved the fluorescence quantum efficiency of the oligomers. Carbazole oligomers without pyrene were found to be suitable as hole-transporting materials, while pyrene-modified oligomers exhibited both light-emitting and hole-transporting properties, making them promising materials for OLED applications. Key chemicals used in the synthesis process included 3-iodo-9H-carbazole, 1-ethynylpyrene, 1,8-diethynylpyrene, and various other intermediates derived from carbazole, as well as palladium and copper catalysts for the Sonogashira coupling reactions that formed the ethynylene linkages.

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

10.1021/jo9002536

The research explores the synthesis of carbazoles using rhodium(II) catalysis. The purpose of this study is to develop an efficient and versatile method for synthesizing carbazoles, which are important heterocyclic compounds with applications in pharmaceuticals and materials science. The key chemicals used in this research include various biaryl azides as starting materials, rhodium(II) complexes such as Rh2(O2CC3F7)4 and Rh2(O2CC7H15)4 as catalysts, and molecular sieves to enhance reaction efficiency. The study concludes that the Rh2(II)-catalyzed method provides a straightforward route to carbazoles with good yields and regioselectivity. The researchers optimized reaction conditions, including temperature, solvent, and catalyst loading, to achieve high efficiency. They also explored the scope of the method by synthesizing a range of carbazoles with different substituents, demonstrating the versatility of the approach. The findings suggest that this method could be a valuable addition to the toolkit for carbazole synthesis, particularly for the preparation of complex carbazole derivatives.

Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow

10.1002/chem.201502661

The study focuses on the photochemical synthesis of complex carbazoles, which are important in pharmaceuticals and materials science, by examining the effects of electronic properties in both UV- and visible-light-mediated reactions under continuous-flow conditions. The researchers used various triarylamines with differing electronic properties, including electron-rich and electron-poor substituents, as well as nitrogen-based heterocycles and halogen-containing arenes. These chemicals served as precursors in the synthesis of carbazoles, and their electronic properties influenced the reaction yields and regiochemical preferences. The purpose of the study was to evaluate the efficiency of photochemical methods for carbazole synthesis and to explore the complementary nature of UV-light and visible-light (photoredox) methods in preparing complex heterocycles. The study also aimed to understand the impact of different substituents on the reaction outcomes, which could inform the development of more efficient synthetic strategies for carbazoles.

Structural studies of some push-pull N-arylbenzazoles

10.1039/c0dt00029a

The research focuses on the structural studies of push-pull N-arylbenzazoles, which are a series of compounds with a benzazole core and an N-aryl group bearing a strong electron-withdrawing group in the 2-position of the N-aryl ring. The purpose of the study was to analyze the X-ray crystal structures and calculated structures of these compounds to understand how they cope with the competing influences of push-pull conjugation and steric hindrance. The chemicals used in the process included carbazoles, indoles, benzimidazoles, and indazoles, with electron-withdrawing groups such as carbomethoxy and nitro groups, and various solvents and reagents for synthesis and analysis, such as formic acid, anhydrous potassium carbonate, and DMF.

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

10.1002/jhet.5570340327

The research aims to explore the chlorination of carbazole and its derivatives to synthesize and isolate various chlorocarbazoles. N-Chlorobenzotriazole is highlighted for its efficiency in chlorination reactions. When used in dichloromethane, it provides high yields of specific chlorocarbazoles. N-Chlorosuccinimide is another key chlorinating agent used in the study. It is employed both in glacial acetic acid and in combination with silica gel in dichloromethane. The study shows that N-chlorosuccinimide in glacial acetic acid provides 1,6-dichlorocarbazole (1c) with a yield of 62%, which is significantly higher than previously reported yields. Both reagents are compared in terms of their efficiency and selectivity. N-chlorobenzotriazole is found to be more selective and efficient for higher chlorinated derivatives, while N-chlorosuccinimide is effective for the formation of 1,6-dichlorocarbazole. The study concludes that both reagents are valuable tools for the chlorination of carbazoles, with their specific advantages depending on the desired chlorocarbazole product and reaction conditions.

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