18992-85-3

Usage

Uses

Used in Organic Synthesis:
3-methoxy-9H-carbazole is used as a building block in the synthesis of organic materials and pharmaceuticals due to its unique chemical properties and reactivity.
Used in Optoelectronic Devices:
3-methoxy-9H-carbazole is used as an electron-transporting material in organic light-emitting diodes (OLEDs) and other optoelectronic devices, leveraging its electron-transporting properties.
Used in Medicinal Chemistry:
3-methoxy-9H-carbazole is used as a compound of interest in the field of medicinal chemistry due to its potential biological activities, such as its antiproliferative and anti-inflammatory properties.

InChI:InChI=1/C13H11NO/c1-15-9-6-7-13-11(8-9)10-4-2-3-5-12(10)14-13/h2-8,14H,1H3

Upstream product

• 13070-45-6 6-Methoxy-1,2,3,4-tetrahydrocarbazole 
• 67-56-1 methanol 
• 21865-50-9 6-bromo-1,2,3,4-tetrahydro-9H-carbazole 
• 107816-54-6 4-[N-(4-methoxyphenyl)amino]benzaldehyde 
• 91902-00-0 2-azido-5-methoxy-1,1'-biphenyl 
• 91901-16-5 5-methoxy-2-nitro-1,1'-biphenyl 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 
• 1592-95-6 3-bromo-9H-carbazole 
• 124-41-4 sodium methylate 
• 53595-99-6 2-chloro-N-(4-methoxyphenyl)aniline 
• 104-94-9 4-methoxy-aniline 
• 95-50-1 1,2-dichloro-benzene 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 191348-14-8 2-iodo-4-methoxylaniline 

Downstream Products

• 7384-07-8 3-Hydroxycarbazol 
• 51145-61-0 1,2,3,4-tetrahydrocarbazol-3-one 
• 52602-27-4 3-hydroxy-9-methylcarbazole 
• 1427160-90-4 4,4'-((2,3,5,6-tetramethyl-4-(6-methoxy-9-methyl-9H-carbazol-3-yl)phenyl) boranediyl)bis(2,3,5,6-tetramethylbenzonitrile) 
• 1612774-87-4 C₂₅H₂₀N₂O 
• 1417618-07-5 3-methoxy-9-phenyl-9H-carbazole 

Relevant academic research and scientific papers

A simple strategy to achieve efficient thermally activated delayed fluorescent emitters via enhancing electron donating ability of donors

Simultaneously achieving both effective reverse intersystem crossing (RISC) process and high values of radiative decay rate (kr)/photoluminescent quantum yield (PLQY) are critical for efficient thermally activated delayed fluorescent (TADF) emitters. The separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) through typical molecular geometry tuning method guarantees a small ΔEST but results in disfavored oscillator strength for fluorescent decay. Herein, a simple method is provided to facilitate the reverse intersystem crossing (RISC) of TADF emitters via enhancing electron donating property of donors rather than twisting the donor-acceptor configuration. Three molecules, namely Me-Cz, Me-MOC and Me-DOC, are designed and synthesized. The introduction of methoxy group enhances the electron-donating ability of carbazole. The stabilized charge transfer state features a reduced splitting energy between the first singlet and triplet excited state, thus activating TADF process. Consequently, the molecules Me-DOC and Me-MOC achieve good external quantum efficiency of 18.6% and 12.4% in electroluminescent devices.

Synthesis and resolution of BICOL, a carbazole analogue of BINOL

The synthesis and resolution of a novel chiral C2-symmetric bicarbazolediol (BICOL), is reported. The key step in the synthesis is the copper(II)-catalysed oxidative phenol coupling of 3-hydroxycarbazole. Menthyl chloroformate is used as resolv

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.

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.

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.

NEW POLYMERIZABLE LIQUID CRYSTAL HAVING A CARBAZOLE CORE

The invention relates to novel anisotropic compounds of formula (I) as well as to liquid crystalline mixtures, films and electro-optical devices comprising the compound.

Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths

The photodecomposition of azides to generate nitrenes usually requires wavelengths in the 300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.

CARBAZOLE OXIME ESTER DERIVATIVE COMPOUND, AND PHOTOPOLYMERIZATION INITIATOR AND PHOTOSENSITIVE COMPOSITION CONTAINING THE SAME

PROBLEM TO BE SOLVED: To provide a carbazole oxime ester derivative compound having excellent sensitivity, heat resistance, chemical resistance and curability, and a photopolymerization initiator and a photosensitive composition containing the same. SOLUT

Asymmetric oxidative coupling of hydroxycarbazoles: Facile synthesis of (+)-bi-2-hydroxy-3-methylcarbazole

Asymmetric oxidative coupling reactions of hydroxycarbazoles have been established using a chiral dinuclear vanadium complex. To demonstrate the utility of vanadium-catalyzed reactions, we have used them to synthesize (+)-bi-2-hydroxy-3-carbazole in three steps from cyclohexanone and commercially available aniline derivatives.

Biphilic Organophosphorus-Catalyzed Intramolecular Csp2-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations

A small-ring phosphacycloalkane (1,2,2,3,4,4-hexamethylphosphetane, 3) catalyzes intramolecular C-N bond forming heterocyclization of o-nitrobiaryl and -styrenyl derivatives in the presence of a hydrosilane terminal reductant. The method provides scalable access to diverse carbazole and indole compounds under operationally trivial homogeneous organocatalytic conditions, as demonstrated by 17 examples conducted on 1 g scale. In situ NMR reaction monitoring studies support a mechanism involving catalytic PIII/PV=O cycling, where tricoordinate phosphorus compound 3 represents the catalytic resting state. For the catalytic conversion of o-nitrobiphenyl to carbazole, the kinetic reaction order was determined for phosphetane catalyst 3 (first order), substrate (first order), and phenylsilane (zeroth order). For differentially 5-substituted 2-nitrobiphenyls, the transformation is accelerated by electron-withdrawing substituents (Hammett factor ? = +1.5), consistent with the accrual of negative charge on the nitro substrate in the rate-determining step. DFT modeling of the turnover-limiting deoxygenation event implicates a rate-determining (3 + 1) cheletropic addition between the phosphetane catalyst 3 and 2-nitrobiphenyl substrate to form an unobserved pentacoordinate spiro-bicyclic dioxazaphosphetane, which decomposes via (2 + 2) cycloreversion giving 1 equiv of phosphetane P-oxide 3·[O] and 2-nitrosobiphenyl. Experimental and computational investigations into the C-N bond forming event suggest the involvement of an oxazaphosphirane (2 + 1) adduct between 3 and 2-nitrosobiphenyl, which evolves through loss of phosphetane P-oxide 3·[O] to give the observed carbazole product via C-H insertion in a nitrene-like fashion.