61166-04-9

Basic information

• Product Name: 9-Methyl-3-aminocarbazole
• Synonyms: 3-Amino-9-methyl-9H-carbazole;3-Amino-9-methylcarbazole;9-Methyl-3-aminocarbazole;9-Methylcarbazol-3-amine;9-methyl-9H-carbazol-3-amine
• CAS NO: 61166-04-9
• Molecular Formula: C₁₃H₁₂N₂
• Molecular Weight: 196.24778
• Mol File: 61166-04-9.mol

Chemical Properties

• Melting Point: 174 °C
• Boiling Point: 415.4°Cat760mmHg
• Flash Point: 205°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 4.13E-07mmHg at 25°C
• Refractive Index: 1.664
• PKA: 4.99±0.30(Predicted)
• CAS DataBase Reference: 9-Methyl-3-aminocarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Methyl-3-aminocarbazole(61166-04-9)
• EPA Substance Registry System: 9-Methyl-3-aminocarbazole(61166-04-9)

Safety Data

• Hazardous Substances Data: 61166-04-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H12N2/c1-15-12-5-3-2-4-10(12)11-8-9(14)6-7-13(11)15/h2-8H,14H2,1H3

Upstream product

• 61166-05-0 9-methyl-3-nitro-9H-carbazole 
• 86-74-8 9H-carbazole 
• 3077-85-8 3-Nitro-carbazol 
• 1484-12-4 N-methylcarbazole 
• 17754-68-6 N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine 

Downstream Products

• 1353648-61-9 ethyl 4-(9-methyl-9H-carbazol-3-ylamino)-2-(4-nitrophenyl)-5-oxo-2,5-dihydro-3-furancarboxylate 
• 1234193-61-3 7-methyl-1,3-diphenyl-7H-pyrido[2,3-c]carbazole 

Relevant articles and documents

Carbazole-decorated fluorescent CdS quantum dots: A potential light-harvesting material

An organic-inorganic nanohybrid system (AMC-CdS QD) comprised of a fluorescent carbazole analog, AMC (3-amino-N-methyl carbazole), and CdS QDs has been synthesized, which shows promise as a sustainable energy harvesting material. FT-IR and 1H NMR spectroscopy have ascertained the covalent grafting of the carbazole moieties onto the mercaptopropionic acid (MPA)-capped surface of the CdS QDs. Detailed photophysical characterization of this nanohybrid system have confirmed the occurrence of efficient F?rster resonance energy transfer (FRET) from its organic to inorganic counterpart. This phenomenon was also demonstrated using SCC-DFTB-based quantum chemical calculations. As explored in the present work, the photoelectron transfer efficiency of AMC-CdS QDs signifies their plausible future applications as light-harvesting materials.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Synthesis of Novel 3-N-substituted Carbazole Derivatives and Evaluation of their Abilities to Inhibit Platelet Aggregation

The carbazole moiety exhibits various biological activities, including anticancer, antiviral, anti-inflammatory, and antimicrobial activities; some compounds containing the moiety also inhibit platelet aggregation. In the present study, we synthesized a series of 3-N-substituted carbazole derivatives and evaluated their abilities to inhibit in vitro platelet aggregation induced by collagen (5 μg/mL). Of the synthesized compounds, compound 5q (JSCa15), with a urea linkage within the carbazole framework, exhibited the strongest inhibitory activity (98.25% at 30 μM). Interestingly, reduction of the nitro group of compound 5q to an amine exhibited significantly decreased activity (compound 5r, 5.18% at 30 μM). Also, substitution of the urea moiety of compound 5q with a carbamate moiety resulted in a considerable loss of activity (compound 8a, 5.91% at 30 μM). These results suggest that the urea moieties and nitro groups of 3-N-substituted carbazole derivatives may play key roles in inhibiting in vitro platelet aggregation induced by collagen.

Non-deprotonative primary and secondary amination of (hetero)arylmetals

Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-NHR) to heteroaryl-as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or Erecting groups. This one-pot transformation allows unprecedented functional group tolerance and it is wellsuited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper (l) salt is required.

1-CYANO-PYRROLIDINE DERIVATIVES AS INHIBITORS OF USP30.

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylatingenzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C- terminal hydrolase 30 or Ubiquitin Specific Peptidase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of conditions involving mitochondrial dysfunction and cancer. Compounds of the invention include compounds having the formula (I) (I) or a pharmaceutically acceptable salt thereof, wherein R1, R 2, R 3, m, L and X are as defined herein.

3-Aminocarbazole Compounds, Pharmaceutical Composition Containing the Same and Method for the Preparation Thereof

A compound of formula (I), in which R1, R2, R3, R4, R5, R6, X and Y have the meanings indicated in the description, and the pharmaceutically acceptable salts thereof. A pharmaceutical composition containing a compound of formula (I) or a pharmaceutically acceptable salt thereof. A method for preparing the abovementioned compound of formula (I) and the pharmaceutically acceptable salts thereof.

3-AMINOCARBAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AND METHOD FOR THE PREPARATION THEREOF

A compound of formula (I), in which R1 , R2, R3, R4, R5, R6, X and Y have the meanings indicated in the description, and the pharmaceutically acceptable salts thereof. A pharmaceutical composition containing a compound of formula (I) or a pharmaceutically acceptable salt thereof. A method for preparing the abovementioned compound of formula (I) and the pharmaceutically acceptable salts thereof.

Structure-activity relationships in a series of NPY Y5 antagonists: 3-Amido-9-ethylcarbazoles, core-modified analogues and amide isosteres

Beginning with carbazole 1a, the amide and alkyl substituents were optimized to maintain potency while adding solubilizing groups. Efforts to replace the 3-amino-9-ethylcarbazole core, a known carcinogen, used the SAR generated in the carbazole series for guidance and led to the synthesis of a number of core-modified analogues. In addition, an isosteric series, in which the amide was replaced with an imidazole, was prepared. Two potent new series lacking the putative toxicophore were identified from these endeavors.

Lithiation of pivaloylamino derivatives of dibenzofuran and 9-methylcarbazole

2-, 3- and 4-Pivaloylamino derivatives of dibenzofuran [compounds (5), (4) and (6), respectively] and analogous 3-, 2- and 1-substituted derivatives of 9-methylcarbazole [compounds (8), (7) and (9), respectively] were subjected to lithiation at 0°C and subsequent reaction with dimethylformamide. Aldehyde formation took place at positions α to δ to the heteroatom as follows: α for (4) and (7); δ for (5); δ and β (3 : 1) for (8); and α′ (6). No formylation occurred with (9).

An expedient synthesis of 5,11-dimethylindolo[3,2-b]-carbazole, a potent ligand for the receptor for TCDD

A new and efficient synthesis has been developed for the title indolocarbazole which has been indicated by a recent computer-aided study to be a potent ligand for the receptor for the naturally occurring carcinogen, TCDD.