4630-20-0

Usage

Uses

Used in Dye and Pigment Production:
3-Methylcarbazole is utilized as a key component in the production of dyes and pigments, contributing to their color and stability. Its chemical properties allow for the creation of a wide range of colorants used in various industries.
Used in Organic LED Material Manufacturing:
3-METHYLCARBAZOLE serves as a crucial material in the development of organic light-emitting diodes (OLEDs), known for their efficiency and potential applications in display technologies and lighting.
Used as an Antioxidant:
3-Methylcarbazole is employed as an antioxidant, which helps in preventing oxidation in various chemical processes and products, thereby enhancing their shelf life and performance.
Used in Pharmaceutical Synthesis:
As a reactant in the synthesis of pharmaceuticals, 3-Methylcarbazole plays a significant role in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Electronics and Photovoltaics:
3-Methylcarbazole is used in the electronics industry for its potential applications in improving the performance of electronic devices, as well as in photovoltaics for enhancing the efficiency of solar cells.
Used as a Catalyst in Organic Synthesis Reactions:
3-METHYLCARBAZOLE functions as a catalyst, facilitating various organic synthesis reactions, thereby speeding up the process and improving the yield of desired products in the chemical industry.

InChI:InChI=1/C13H11N/c1-9-6-7-13-11(8-9)10-4-2-3-5-12(10)14-13/h2-8,14H,1H3

Upstream product

• 78766-51-5 1-(4-methylphenyl)-1H-benzo[d][1,2,3]triazole 
• 38504-76-6 5-methyl-1-phenyl-1H-1,2,3-benzotriazole 
• 17177-17-2 6-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 5257-08-9 3-methyl-6-hydroxycarbazol 
• 620-84-8 4-methyldiphenylamine 
• 76943-49-2 4-methylphenyl 2-azidobenzoate 
• 58005-42-8 6-hydroxy-2-methoxy-3-methyl-9H-carbazole 
• 91901-93-8 2-azido-5-methyl-1,1'-biphenyl 
• 33634-03-6 1-(3-methyl-9H-carbazol-9-yl)ethanone 
• 885527-46-8 1-p-tolyl-1H-benzotriazole-5-carboxylic acid 
• 91-22-5 quinoline 
• 861317-20-6 1-p-toluidino-cyclopentanecarboxylic acid 
• 141-52-6 sodium ethanolate 
• 211106-13-7 6,7-dimethoxy-1-hydroxy-3-methylcarbazole 

Downstream Products

• 24075-48-7 3,9-dimethyl-9H-carbazole 
• 69633-36-9 8-formyl-3-methylcarbazole 
• 132921-83-6 6-formyl-3-methylcarbazole 
• 132921-82-5 1-formyl-3-methylcarbazole 
• 51761-07-0 9H-carbazole-3-carbaldehyde 
• 14960-81-7 1-hydroxy-3-methyl-9H-carbazole 
• 24224-30-4 2-hydroxy-3-methyl-9H-carbazole 
• 83482-65-9 C₂₆H₁₈N₂O 
• 83482-62-6 3-formyl-6-hydroxycarbazole 
• 100108-66-5 murrayaquinone A 
• 51035-17-7 9H-carbazole-3-carboxylic acid 
• 86-74-8 9H-carbazole 
• 115552-50-6 9-benzenesulfonyl-3-carbazolecarboxaldehyde 
• 54736-01-5 3-dibromomethyl-9-benzenesulfonylcarbazole 

Relevant academic research and scientific papers

MUKONICINE, A CARBAZOLE ALKALOID FROM LEAVES OF MURRAYA KOENIGII

A new carbazole alkaloid, mukonicine, was isolated from the leaves of Murraya koenigii.From physical methods coupled with chemical evidence its structure was determined as 1,2-3-pyrano>-3-methyl-6,8-dimethoxycarbazole. - Key Word Index: Murraya koenigii; Rutaceae; mukonicine; carbazole alkaloid.

GLYCOZOLININE, A CARBAZOLE DERIVATIVE FROM GLYCOSMIS PENTAPHYLLA

Key Word Index - Glycosmis pentaphylla; Rutaceae; seeds; alkaloids; glycozolinine; carbazole. A new carbazole derivative, glycozolinine, was isolated from the seeds of Glycosmis pentaphylla.From physical and chemical evidence its structure is 6-hydroxy-3-methylcarbazole.

Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions

Self-assembled multilayer iron(0) nanoparticles (NPs, 6-10 nm), namely, sulfur-modified Au-supported Fe(0) [SAFe(0)], were developed for ligand-free one-pot carbon-carbon/carbon-nitrogen bond-forming reactions. SAFe(0) was successfully prepared using a well-established metal-nanoparticle catalyst preparative protocol by simultaneous in situ metal NP and nanospace organization (PSSO) with 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (Si-DHP) as a strong reducing agent. SAFe(0) was easy to handle in air and could be recycled with a low iron-leaching rate in reaction cycles.

Dearomatization-Rearomatization Strategy for Synthesizing Carbazoles with 2,2′-Biphenols and Ammonia by Dual C(Ar)-OH Bond Cleavages

Carbazole is an essential building block in various pharmaceuticals, agrochemicals, natural products, and materials. For future sustainability, it is highly desirable to synthesize carbazole derivatives directly from renewable resources or cheap raw materials. Phenolic compounds are a class of degradation products of lignin. On the other hand, ammonia is a very cheap industrial inorganic chemical. Herein, an efficient dearomatization-rearomatization strategy has been developed to directly cross-couple 2,2′-biphenols with ammonia by dual C(Ar)-OH bond cleavages. This strategy provides a greener pathway to synthesize valuable carbazole derivatives from phenols.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

Substituent-Guided Palladium-Ene Reaction for the Synthesis of Carbazoles and Cyclopenta[ b]indoles

An efficient palladium-catalyzed intramolecular Trost-Oppolzer type Alder-ene strategy was developed for the synthesis of carbazoles and cyclopenta[b]indoles from easily accessible(3-allyl-1H-indol-2-yl)methyl acetates. This strategy was extended for the synthesis of naphthalenes and dibenzobenzofurans as well. In addition, a short synthesis of antibacterial and antifungal natural product glycozoline and its analogues was also achieved.

Substituent-Guided Palladium-Ene Reaction for the Synthesis of Carbazoles and Cyclopenta[b]indoles

An efficient palladium-catalyzed intramolecular Trost-Oppolzer type Alder-ene strategy was developed for the synthesis of carbazoles and cyclopenta[b]indoles from easily accessible(3-allyl-1H-indol-2-yl)methyl acetates. This strategy was extended for the synthesis of naphthalenes and dibenzobenzofurans as well. In addition, a short synthesis of antibacterial and antifungal natural product glycozoline and its analogues was also achieved.

Visible-light-promoted intramolecular C-H amination in aqueous solution: Synthesis of carbazoles

An effective and operationally simple protocol is reported for the synthesis of versatile carbazoles. With water as a co-solvent, visible-light rather than various metals is used to facilitate the conversion of readily available 2-azidobiphenyls under mild conditions. Various functionalized bioactive natural alkaloids, such as glycoborine, clausine C, clausine L, clausine H and clauszoline K, were synthesized efficiently with nitrogen as a sole byproduct. The reaction could be performed in water, acidic or alkaline buffer solutions, showing its potential for applications in biochemistry.

Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids

An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.