6510-65-2

Usage

Uses

Used in Dye and Pigment Production:
1-methyl-9H-carbazole is utilized as a key intermediate in the synthesis of dyes and pigments, contributing to the vibrant coloration and stability of these products in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1-methyl-9H-carbazole serves as a crucial component in the development of new drugs, leveraging its chemical properties to enhance the efficacy and safety of medicinal compounds.
Used in Organic Light-Emitting Diodes (OLEDs):
1-methyl-9H-carbazole is employed as a material in the fabrication of OLEDs, where its unique properties contribute to the device's light-emitting characteristics and overall performance.
Used as an Antioxidant in Materials:
1-methyl-9H-carbazole is also used as an antioxidant in various materials, where it helps to prevent oxidation and degradation, thereby extending the lifespan and maintaining the quality of the products.
Overall, 1-methyl-9H-carbazole is a multifaceted chemical with applications spanning across different industries, from the production of dyes and pharmaceuticals to the development of advanced materials and technologies such as OLEDs.

Upstream product

• 120-72-9 indole 
• 3209-78-7 5,5-dimethoxy-pentan-2-one 
• 17058-12-7 1-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 725234-49-1 1-o-toluidino-cyclopentanecarboxylic acid 
• 19283-51-3 8-Methyl-1,2,3,4-tetrahydro-carbazol 
• 64-19-7 acetic acid 
• 1208-57-7 2-methylcyclohexanone phenylhydrazone 
• 854715-10-9 cyclohexanone-o-tolylhydrazone 
• 3449-50-1 8-methyl-2,3,4,9-tetrahydro-carbazol-1-one 
• 77-77-0 Divinyl sulfone 
• 35296-53-8 1-methylpyrano[3,4-b]indol-3(9H)-one 
• 5535-48-8 PVS 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 63075-50-3 cyclohexanone 2-ethyl-6-methylphenylhydrazone 

Downstream Products

• 86-74-8 9H-carbazole 
• 6311-19-9 9H-carbazole-1-carboxylic acid 
• 1903-94-2 9H-carbazole-1-carbaldehyde 
• 21240-57-3 3-formyl-1-methylcarbazole 

Relevant academic research and scientific papers

Secondary phosphine oxides assisted palladium complexes catalyzed catellani reaction for the formation of carbazole derivatives

Several secondary phosphine oxides (SPOs, 2a-2d) as well as 2a-chelated palladium complex 2a_Pd were employed in Catellani type reaction for the synthesis of 1-methyl-9H-carbazole (4) from 2-iodotoluene and N-(2-bromophenyl)acetamide (3). The application

Synthesis of Carbazoles from 2-Iodobiphenyls by Palladium-Catalyzed C?H Activation and Amination with Diaziridinone

A facile and efficient approach has been developed for the synthesis of carbazoles from 2-iodobiphenyls and diaziridinone under palladium catalysis. A wide range of carbazoles were synthesized in good to excellent yields, and indole derivatives were obtained by using styrenes as the substrate. The palladacycles obtained from 2-iodobiphenyls acted as the key intermediate, and the reaction should proceed via a tandem Pd-catalyzed C?H activation/dual C?N bond formation sequence. (Figure presented.).

A versatile carbazole donor design strategy for blue emission switching from normal fluorescence to thermally activated delayed fluorescence

The weak electron donating ability of carbazole is most suitable for constructing the donor-acceptor type blue emitters, but its low spatial requirements caused by the five-membered ring bridged structure is not favorable for spatial separation of frontier molecular orbitals. So many carbazole based compounds do not exhibit thermally activated delayed fluorescence (TADF). Herein, a more sterically demanding group was introduced at the 1-site of carbazole to form 1-methylcarbazole (1-MeCz), in order to construct a versatile donor for blue TADF materials. 1-MeCz was used as donor in combination with triazine and pyrimidine as acceptors to design novel compounds 1-MeCz-TRZ and 1-MeCz-Pm. It was observed that the presence of the methyl group at the 1-site of carbazole enhanced the twisted angles and reduced frontier molecular orbital overlapping, successfully switching the blue emission from the normal fluorescence of the methyl-free reference compounds (Cz-TRZ and Cz-Pm) to TADF of 1-MeCz-TRZ and 1-MeCz-Pm. The organic light-emitting diodes of 1-MeCz-TRZ and 1-MeCz-Pm exhibited blue emission at 450 and 458 nm with Commission Internationale de L'Eclairage (CIE) coordinates of (0.15, 0.11) and (0.17, 0.18), and external quantum efficiencies of 13.07% and 7.53%. This study provides a versatile, simple and practical design strategy with 1-MeCz to construct pure blue TADF emitters in combination with various acceptors.

Stereospecific access to bridged [n.2.1] skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides

An efficient gold-catalyzed anti-Markovnikov cycloisomerization-initiated tandem reaction of Boc-protected indole tethered homopropargyl amides has been achieved. This method delivers a wide range of valuable bridged aza-[n.2.1] skeletons (n = 3–7) at room temperature with high diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the gold-catalyzed tandem reaction of homopropargyl alcohol is also achieved to produce the bridged oxa-[3.2.1] skeleton.

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.

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.

Photochemical intramolecular amination for the synthesis of heterocycles

Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.

Preparation of Secondary Phosphine Oxide Ligands through Nucleophilic Attack on Imines and Their Applications in Palladium-Catalyzed Catellani Reactions

Several new amino-type secondary phosphine oxide (SPO) pre-ligands (3a–3h) that contain P–N bonds were synthesized and characterized. SPOs 3a–3h can tautomerize to phosphinous acids (PA, 3a–3h) as genuine ligands. The formation of SPOs 3a–3h occurred first through nucleophilic attack on the imine carbon atom, then by the addition of RPCl2(R = Ph, Cy, tBu, or iPr), and work-up under acidic conditions. The P–N bond in the newly prepared SPOs is evident from the crystal structures of SPOs 3d and 3h. Reactions of SPOs 3f, 3g, or 3h with Pd(COD)Cl2(COD = cyclooctadiene) yielded palladium complexes 6f, 6g, or 6h. In these crystal structures, PAs 3f, 3g, and 3h act as didentate ligands through P and N donors. Intriguingly, the reaction of SPO 3f with Pd(COD)Cl2also gave rise to palladium complexes 7fa, 7fb, and 8f. The crystal structures of 7fa and 7fb show that the palladium atom is chelated by PA 3f and coordinated by a phosphine-like ligand fragmented from SPO 3f through C–N bond dissociation. Finally, the syntheses of carbazole derivatives were pursued in Catellani reactions with SPOs 3g and 3h as pre-ligands. A mechanism is proposed to account for the catalytic reaction (see the Supporting Information). The optimized conditions for Suzuki reactions using selected SPO ligands are also reported.

Palladium-Catalyzed Intramolecular C–H Amination in Water

Palladium(II) catalysis was found to be effective for intramolecular C–H amination in water. With 2-azidobiphenyls as substrates, the reaction efficiently provided various carbazoles with N2as the sole byproduct. The reaction showed high functional-group tolerance and could be used in the synthesis of several natural carbazole alkaloids. The catalytic process was promoted by water, and the reaction was inefficient in the organic solvents that were investigated.

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).