17223-85-7

Usage

Uses

Used in Organic Dyes and Pigments Industry:
9-Aminocarbazole is used as a key intermediate in the synthesis of organic dyes and pigments, contributing to the development of colorants with enhanced properties such as stability and color intensity.
Used in Pharmaceutical Industry:
9-Aminocarbazole is utilized as a building block in the production of pharmaceuticals, leveraging its potential antitumor and antiviral activities to develop new therapeutic agents for various diseases.
Used in Agrochemical Industry:
9-Aminocarbazole is employed as a component in the formulation of agrochemicals, such as pesticides and herbicides, due to its potential to enhance the effectiveness of these products.
Used in Medicinal Chemistry Research:
9-Aminocarbazole is used as a subject of interest in medicinal chemistry research, where its antitumor and antiviral properties are explored for the development of novel therapeutic agents and treatments.

InChI:InChI=1/C12H10N2/c13-14-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14/h1-8H,13H2

Upstream product

• 86-74-8 9H-carbazole 
• 31438-20-7 9-nitro-9H-carbazole 
• 2788-23-0 9-nitroso-9H-carbazole 
• 60-29-7 diethyl ether 
• 64-19-7 acetic acid 

Downstream Products

• 71851-86-0 benzylidene-carbazol-9-yl-amine 
• 76604-05-2 salicylaldehyde-carbazol-9-ylimine 
• 96073-54-0 1-carbazol-9-yl-3,3-diphenyl-azetidine-2,4-dione 
• 71851-87-1 carbazol-9-yl-cinnamyliden-amine 
• 76591-31-6 carbazol-9-yl-(1-phenyl-ethyliden)-amine 
• 21046-05-9 9-[(2,4,6-trinitrophenyl)amino]carbazole 
• 104636-53-5 1-phenyl-9H-carbazole 
• 103012-26-6 3-phenyl-9H-carbazole 
• 1192179-05-7 C₃₁H₁₃BF₁₀N₂ 
• 71903-22-5 N-(9H-carbazol-9-yl)-4-methylbenzeneamine 

Relevant academic research and scientific papers

Carbazolyl nitrenium cations: Generation and reactions

Carbazolyl nitrenium cations were generated during the thermolysis and photolysis of 1-carbazol-9-yl-2,4,6-triphenylpyridinium (Py+-Cz) tetrafluoroborate in 2,2,2-trifluoroethanol- and TFA - mesitylene mixtures. The thermolysis of Py+-Cz in TFA-mesitylene mixture gave 9-mesitylcarbazole in good yield along with carbazole, non-symmetrical mesitylene dimer, 2,4,6-triphenylpyridine, and a small amount of 9-(3,5-dimethylbenzyl)carbazole, whereas the thermolysis in trifluoroethanol - mesitylene mixture gave 9-mesitylcarbazole as the main product along with carbazole and 2,4,6-triphenylpyridine. The product distributions lead to two major conclusions. First, photolysis and thermolysis of Py+-Cz salt produce nitrenium ions that can be in singlet or triplet state dependant on the reaction conditions. Second, the carbazolyl nitrenium ion exhibits singlet state in the ground state.

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.

SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME

The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts, solvates and prodrugs thereof: Formula (I) wherein Q is selected from O, S and Se; J is S or Se; W1 and W2, when present, are independe

Groups 5 and 6 terminal hydrazido(2-) complexes: Nβ substituent effects on ligand-to-metal charge-transfer energies and oxidation states

Brightly colored terminal hydrazido(2-) (dme)MCl3(NNR 2) (dme = 1,2-dimethoxyethane; M = Nb, Ta; R = alkyl, aryl) or (MeCN)WCl4(NNR2) complexes have been synthesized and characterized. Perturbing the electronic environment of the β (NR 2) nitrogen affects the energy of the lowest-energy charge-transfer (CT) transition in these complexes. For group 5 complexes, increasing the energy of the Nβ lone pair decreases the ligand-to-metal CT (LMCT) energy, except for electron-rich niobium dialkylhydrazides, which pyramidalize Nβ in order to reduce the overlap between the Nb=N α π bond and the Nβ lone pair. For W complexes, increasing the energy of Nβ eventually leads to reduction from formally [WVI≡N-NR2] with a hydrazido(2-) ligand to [WIV=N=NR2] with a neutral 1,1-diazene ligand. The photophysical properties of these complexes highlight the potential redox noninnocence of hydrazido ligands, which could lead to ligand- and/or metal-based redox chemistry in early transition metal derivatives.

Synthesis and structure-activity relationships of N-propyl-N-(4- pyridinyl)-1H-indol-1-amine (besipirdine) and related analogs as potential therapeutic agents for Alzheimer's disease

A series of novel N-(4-pyridinyl)-1H-indol-1-amines and other heteroaryl analogs was synthesized and evaluated in tests to determine potential utility for the treatment of Alzheimer's disease. From these compounds, N-propyl-N- (4-pyridinyl)-1H-indol-1-amine (besipirdine, 4c) was selected for clinical development based on in-depth biological evaluation. In addition to cholinomimetic properties based initially on in vitro inhibition of [3H]quinuclidinyl benzilate binding, in vivo reversal of scopolamine- induced behavioral deficits, and subsequently on other results, 4c also displayed enhancement of adrenergic mechanisms as evidenced in vitro by inhibition of [3H]clonidine binding and synaptosomal biogenic amine uptake, and in vivo by reversal of tetrabenazine-induced ptosis. The synthesis, structure-activity relationships for this series, and the biological profile of 4c are reported.

N-substituted-4-pyrimidinamines and pyrimidinediamines

This invention relates to N-heteroaryl-4-pyrimidinamines of the formula STR1 where R1 is hydrogen, loweralkyl, aryl, or arylloweralkyl; R2 and R3 are independently hydrogen or loweralkyl, or R2 and R3 taken together are aryl; R4 and R5 are independently hydrogen or lowealkyl, or R4 and R5 taken together are aryl; X is hydrogen, halogen, cyano, nitro, amino, loweralkyl, loweralkoxy, trifluoromethyl or STR2 where Y is hydrogen, halogen or loweralkyl; m is an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometrical and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as memory enhancing agents and as analgesic agents.

N-heteroaryl-purin-6-amines useful as analgesic and anticonvulsant agents

This invention relates to a N-heteroaryl-purin-6-amine of the formula STR1 where R1 is hydrogen, lower alkyl, and arylloweralkyl; R2 and R3 are independently hydrogen, lower alkyl or R2 and R3 taken together are aryl; R4 and R5 are independently hydrogen, lower alkyl, or R4 and R5 taken together are aryl; R6 is hydrogen, lower alkyl, aryl, arylloweralkyl, STR2 where R2, R3, R4 and R5 are as defined above, and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometric and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as analgesic and anticonvulsant agents.

Aminations with O-Diphenylphosphinylhydroxylamine. A Critical Evaluation

A critical evaluation is presented of the scope of amination reactions with O-diphenylphosphinylhydroxylamine (ODPH) as compared to those using hydroxylamine-O-sulfonic acid (HOSA).Aminations with ODPH of isopropyl, t-butyl and cyclohexyl carbanions derived from the corresponding Grignard reagents, gave the corresponding amines in 36, 34 and 50 percent yields, respectively.The amination with HOSA of the same carbanions under similar conditions was unsuccessful.The aminative quaternization of the tertiary nitrogen of pyridine and quinoline with ODPH proceeded with comparable yields to those obtained with HOSA.An improved one flask amination with ODPH of indole, skatole and carbazole was achieved in 52 - 62 percent yields.The amination under the same conditions using HOSA gave consistently lower yields.Several other amination reactions which have been reported for HOSA were unsuccessful using ODPH.The conclusion is reached that overall the ODPH reagent is much less versatile than HOSA.Nevertheless, in the aminations of NH groups of heterocyclic compounds ODPH appears to be superior to HOSA and is the reagent of choice, in particular, since the preparation of ODPH is much less harzardous than that of HOSA. - Keywords: Synthesis, O-Diphenylphosphinylhydroxylamine, Hydroxylamine-O-sulfonic Acid, N-Amino Derivatives, N-Amino Heterocyclic Compounds

Crystal and molecular structure of 9-(2,4,6-trinitroanilino)-carbazole, C18H11N5O6

The crystal structure of 9-(2,4,6-trinitroanilino)-carbazole, C18H11N5O6, has been determined by X-ray diffraction.Crystals are monoclinic, space group P21/c, a = 14.686(11), b = 24.601(12), c = 10.047(5) Angstroem, β = 107.76(5) deg at 292 K, with Z = 8.The two nitrogen atoms in the central fragment have a staggered conformation with an N-N distance of 1.381(4) Angstroem, which is considerably shorter than N-N distances in related N-picrylhydrazine molecules.The picryl moiety has a geometry similar to that of related N-picrylhydrazine molecules.The title compound contains an N-H...O intramolecular bond to one of the ortho nitro gro ups on the picryl ring.The carbazole plane of one molecule and the picryl plane of a neighboring molecule overlap to form an infinite linear chain of the form ...DhA:DhA... where D represents the carbazole donor, h the linear chain linkage within the molecule, and A represents the picryl acceptor of one molecule.The two interplanar distances between D of one molecule and A of an adjacent molecule are 3.28(13) and 3.34(13) Angstroem, indicating a strong ?-molecular interaction.

A TRIFLUOROMETHANESULFONIC ACID-CATALYZED REACTION OF ARYLHYDRAZINES WITH BENZENE

Arylhydrazines reacted with benzene in the presence of trifluoromethanesulfonic acid (TFSA) to give aminobiphenyls.This is a general method for the synthesis of aminobiphenyls.