4532-33-6

Usage

Uses

Used in Electronics Industry:
1-Methoxy-3-Methylcarbazole is used as a hole-transport material in the production of OLEDs (organic light-emitting diodes) for its high thermal stability and good film-forming properties, contributing to the efficiency and performance of electronic devices.
Used in Materials Science:
1-Methoxy-3-Methylcarbazole is used in the development of organic semiconductors, photovoltaic devices, and sensors due to its fluorescent properties, enhancing the performance and functionality of these materials.
Used in Biomedicine:
1-Methoxy-3-Methylcarbazole is studied for its potential use as an anticancer agent, exhibiting cytotoxic effects on cancer cells, which could lead to the development of new therapeutic approaches in cancer treatment.

Upstream product

• 67-56-1 methanol 
• 103763-45-7 1-indol-2-yl-3-methylbutane-1,4-dione 
• 16045-88-8 boron trifluoride methanol complex 
• 14960-81-7 1-hydroxy-3-methyl-9H-carbazole 
• 77-78-1 dimethyl sulfate 
• 723-97-7 murrayanine 
• 694-80-4 2-bromo-1-chlorobenzene 
• 39538-68-6 2-methoxy-4-methylaniline 
• 95-50-1 1,2-dichloro-benzene 
• 38512-82-2 3-methoxy-4-nitrotoluene 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 103763-41-3 4-hydroxy-1-indol-2-yl-3-methylbutan-1-one 
• 103763-38-8 4,5-dihydro-3-indol-2-ylcarbonyl-4-methylfuran-2-one 
• 108-86-1 bromobenzene 

Downstream Products

• 14960-81-7 1-hydroxy-3-methyl-9H-carbazole 
• 100108-66-5 murrayaquinone A 
• 723-97-7 murrayanine 
• 89368-89-8 1-methoxy-9-[(1-methoxycarbazol-3-yl)-methyl]-3-methylcarbazole 
• 1397693-64-9 C₃₆H₃₀N₂O₆S 
• 1430117-67-1 9-(3-(4-(3,5-difluorophenyl)-1H-1,2,3-triazol-1-yl)propyl)-1-methoxy-3-methyl-9H-carbazole 
• 1430117-68-2 1-methoxy-3-methyl-9-(3-(4-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl)propyl)-9H-carbazole 
• 1430117-69-3 9-(3-(4-((4-(2,5-difluorobenzyl)piperazin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)propyl)-1-methoxy-3-methyl-9H-carbazole 
• 1430117-65-9 9-((4((tert-butyldiphenylsilyloxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)-1-methoxy-3-methyl-9H-carbazole 

Relevant academic research and scientific papers

DIMERIC MURRAYAFOLINE A, A POTENTIAL BIS-CARBAZOLE ALKALOID: 'BIOMIMETIC' SYNTHESIS, ATROPOISOMER SEPARATION, AND ANTIMALARIAL ACTIVITY

The first total synthesis of a (potential) dimeric carbazole alkaloid is described.After an improved preparation of the monomeric building block, 'biomimetic dimerization' by oxidative phenolic coupling was best achieved with di-tert-butyl peroxide in chlorobenzene, leading to a highly selective formation of the 2,2'-coupled 'dimer', the parent framework of several naturally occurring dimeric carbazole alkaloids.For the atropoenantiomer analysis, a chromatographic procedure on chiral phase was developed.Both the mono- and the dimeric phenolic carbazoles displayed in vitro antimalarial activity against Plasmodium falciparum.

Total synthesis of clausamine e and furanoclausamine B

4-Bromo-1-methoxycarbazole-3-carboxylate has been synthesized by a sequence of benzannulation-decarboxylation-bromination, and utilized as a common intermediate for the first total synthesis of clausamine E and the second synthesis of furanoclausamine B. Heck coupling and Br-Li exchange reactions are, respectively, employed as the key steps.

New syntheses of murrayafoline-A and murrayaquinone-A via Fischer indolization of 2-sulfonyloxyphenylhydrazone (Fischer indolization and its related compounds. Part 29)

Two carbazole alkaloids, murrayafoline-A (4a) and murrayaquinone-A (4b), were synthesized from 1, 2, 3, 4-tetrahydro-8-methanesulfonyloxy-6- methylcarbazole (8) prepared in the application of Fischer indolization of 2- sulfonyloxyphenylhydrazone.

Total synthesis of carbazole alkaloids

A Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-carbazole-1-carboxylic acid methyl ester, (3-methoxy-9H-carbazol-1-yl)-methanol, 3-methoxy-9H-carbazole-1-carbaldehyde, 3-methoxy-9H-carbazole-1-carboxylic acid, 2-methyl-9H-carbazole and nonsteroidal anti-inflammatory drug (NSAID) carprofen and its derivatives.

Palladium-Catalyzed Regioselective Synthesis of 1-Hydroxycarbazoles Under Aerobic Conditions

A palladium-catalyzed aerobic C?H amidation of N-Ts-2-amino-3′-hydroxylbiaryls has been developed to afford a diverse range of 1-hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, a

"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E

We describe the total synthesis of methylene-bridged biscarbazole alkaloids by using a late-stage Ullmann-type coupling of fully functionalised carbazole subunits. The carbazole derivatives were synthesised via a sequence of palladium(0)- and palladium(II

First total synthesis of murrastifoline B and an improved route to murrastifoline F

We report the first total synthesis of murrastifoline B and an improved route to murrastifoline F using a twofold palladium-catalyzed Buchwald-Hartwig amination as key step. The monomeric carbazole and the biaryl precursor are also prepared via palladium-

Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: A combined experimental and computational investigation

A new protocol for the aromatization of tetrahydrocarbazoles has been achieved using a catalytic amount of iodine, giving high yields. The role of iodine in the aromatization has been explained by DFT, and its wide scope is extended to the total synthesis of glycozoline and murrayafoline A. This method has proven to be tolerant of a broad range of functional groups. This journal is the Partner Organisations 2014.

A Pd-catalyzed cascade reaction of N-H insertion and oxidative dehydrogenative aromatization: A new entry to 2-amino-phenols

A palladium-catalyzed cascade reaction of N-H insertion (NHI) and oxidative dehydrogenative aromatization (ODA) has been developed, which affords a straightforward and efficient way to access the carbazole precursors (2-arylamino-phenols) as well as to prepare 2-alkylamino-phenols from non-aromatic substrates. This journal is the Partner Organisations 2014.