1140-50-7

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Dimethyl-9H-carbazol-3-amine is used as a reactant in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic properties.
Used in Dye Industry:
In the dye industry, N,N-Dimethyl-9H-carbazol-3-amine is used as a reactant for the production of various dyes, leveraging its chemical structure to create compounds with specific color characteristics.
Used in Materials Science and Technology:
N,N-Dimethyl-9H-carbazol-3-amine is used as a building block in materials science and technology for its potential to contribute to the development of new materials with unique properties, such as improved conductivity or stability.

Upstream product

• 94127-17-0 Dimethyl-[9-(toluene-4-sulfonyl)-9H-carbazol-3-yl]-amine 
• 3077-85-8 3-Nitro-carbazol 
• 86-74-8 9H-carbazole 
• 1592-95-6 3-bromo-9H-carbazole 
• 506-59-2 N,N-dimethylammonium chloride 
• 62876-66-8 5-dimethylamino-2-nitrobenzoic acid 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 92683-72-2 N-(p-toluenesulfonyl)-3-nitrocarbazole 
• 94127-11-4 3-amino-9-p-toluenesulfonylcarbazole 
• 6377-12-4 3-amino-9H-carbazole 
• 18173-52-9 carbazolyl-3-trimethylammonium iodide 
• 77-78-1 dimethyl sulfate 

Relevant academic research and scientific papers

9-Aryl-3-aminocarbazole as an Environment- and Stimuli-Sensitive Fluorogen and Applications in Lipid Droplet Imaging

Environment-sensitive luminophoric molecules have played an important role in the fields of smart materials, sensing, and bioimaging. In this study, it was demonstrated that depending on the substituents, 9-aryl-3-aminocarbazoles can display aggregation-induced emission and solvatofluorochromism, and the operating mechanism was clarified. The application of these compounds to lipid droplet imaging and fluorescent probes for cysteamine was demonstrated.

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.

N-METHYL DERIVATIVES OF 3-AMINOCARBAZOLE

Methylation of 3-aminocarbazole in presence of sodium hydrogencarbonate yields carbazolyl-3-trimethylammonium iodide, in alkaline media the fourth methyl group is introduced. 3-(N,N-Dimethylamino)-carbazoles were obtained from corresponding methiodides by lithium aluminium hydride reduction or by thermal decomposition.Synthesis of 3-(N-methylamino)-carbazole via tosylamide failed because of 3-(N-methyltosylamino)-9-tosylcarbazole cleaved only one sulfonamide bond.The method involving formylation of 3-aminocarbazole and reduction of the amide gave satisfactory results.