4544-87-0

Usage

Molecular weight

209.24 g/mol The mass of one mole of 1-methoxy-9H-carbazole, measured in grams per mole.

Derivative of carbazole

A heterocyclic aromatic compound 1-Methoxy-9H-carbazole is derived from carbazole, which is a compound containing a ring of atoms with at least one heteroatom (in this case, nitrogen).

Industrial applications

Organic semiconductors, dyes, pigments, and pharmaceuticals The compound is primarily used in the synthesis of organic semiconductors and as a precursor in the production of various dyes, pigments, and pharmaceuticals.

Light sensitivity

Photoconversion devices 1-Methoxy-9H-carbazole is a light-sensitive compound, making it suitable for use in devices that convert light energy into other forms of energy or chemical changes.

Antioxidant and antimicrobial properties

Potential applications in various industries The compound exhibits potential antioxidant and antimicrobial properties, which could make it useful in a range of applications, from food preservation to antimicrobial coatings.

Physical appearance

Pale yellow to off-white solid at room temperature The compound's color and state (solid) at standard room temperature conditions.

Solubility

Soluble in common organic solvents 1-Methoxy-9H-carbazole can dissolve in many organic solvents, which is important for its use in chemical reactions and industrial processes.

Upstream product

• 67-56-1 methanol 
• 615-43-0 2-iodophenylamine 
• 10365-98-7 3-methoxyphenylboronic acid 
• 615-36-1 2-bromoaniline 
• 38089-02-0 3'-methoxy-[1,1'-biphenyl]-2-amine 

Relevant academic research and scientific papers

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.

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.

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.

Iron-Catalyzed Intramolecular C(sp2)-H Amination

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular C-H amination of α-azidobiaryls and (azidoaryl)alkenes into the corresponding carbazoles and indoles, respectively, under mild conditions and with low catalyst loadings. These features and the broad functional-group tolerance render this method a particularly attractive alternative to established noble-metal-based procedures.

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

An array of carbazoles (23 examples) can be synthesized from substituted biaryl azides at 60 °C using substoichio-metric quantities of Rh 2(O2CC3F7)4 or Rh 2(O2CC7H15)4.

Carbazolyl nitrenium ion: Electron configuration and antiaromaticity assessed by laser flash photolysis, trapping rate constants, product analysis, and computational studies

(Graph Presented) Laser flash photolysis of 1-(carbazol-9-yl)-2,4,6- trimethylpyridinium tetrafluoroborate generates the carbazolyl nitrenium ion (τ = 333 ns, kobs = 3.0 × 106 M -1S-1) having absorption bands at 570 and 620 nm in CH3CN. The nitrenium ion is found to have reactivity comparable to structurally similar closed-shell diarylnitrenium ions, but spectroscopic evidence favors an open-shell singlet diradical assignment for the observed nitrenium ion. The carbazolyl nitrenium ion is also more reactive than diarylnitrenium ions as a likely result of antiaromatic character. Ab initio and hybrid DFT calculations were performed to address the degree of antiaromaticity in this and similar nitrenium ions through analysis of optimized geometries, nucleus independent chemical shifts, and isodesmic reactions.