102308-97-4

Basic information

• Product Name: 5-AMINO-1-N-METHYLINDOLE
• Synonyms: TIMTEC-BB SBB010309;1-METHYL-1H-INDOLE-5-YLAMINE;1-METHYL-1H-INDOL-5-AMINE;1-METHYL-1H-INDOL-5-YLAMINE;5-AMINO-1-N-METHYLINDOLE;5-AMINO-N-METHYLINDOLE;5-Amino-1-methyl-1H-indole 97%;1H-Indol-5-amine,1-methyl-(9CI)
• CAS NO: 102308-97-4
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.19
• Product Categories: AMINEPRIMARY;Indole;Heterocycle-Indole series
• Mol File: 102308-97-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: 102 °C
• Boiling Point: 328.036 °C at 760 mmHg
• Flash Point: 152.191 °C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 5.05±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-1-N-METHYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-N-METHYLINDOLE(102308-97-4)
• EPA Substance Registry System: 5-AMINO-1-N-METHYLINDOLE(102308-97-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-36-22-20/21/22
• Safety Statements: 36/37/39-26-22
• RIDADR: 2811
• HazardClass: IRRITANT
• Hazardous Substances Data: 102308-97-4(Hazardous Substances Data)

Usage

Description

5-Amino-1-N-methylindole, with the chemical formula C9H10N2, is an indole derivative and a valuable building block in organic synthesis. It is characterized by a brown solid appearance and possesses a unique molecular structure that includes an amino group and a methylindole moiety. 5-AMINO-1-N-METHYLINDOLE is known for its role in the synthesis of various organic compounds, particularly in the copper-catalyzed synthesis of sulfonamides.

Uses

Used in Pharmaceutical Industry:
5-Amino-1-N-methylindole is used as a key intermediate in the synthesis of sulfonamides, which are a class of antimicrobial agents. These sulfonamides are employed as antibiotics to treat a wide range of bacterial infections, including urinary tract infections, respiratory infections, and skin infections. The copper-catalyzed synthesis of sulfonamides using 5-Amino-1-N-methylindole allows for the development of new and more effective antimicrobial agents.
Used in Organic Synthesis:
5-Amino-1-N-methylindole is used as a versatile building block in organic synthesis for the preparation of various organic compounds. Its unique molecular structure allows for the formation of a wide range of chemical reactions, enabling the synthesis of complex organic molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
5-Amino-1-N-methylindole is used as a research compound in the development of new synthetic methods and reaction pathways. Its reactivity and structural features make it an attractive candidate for exploring novel synthetic routes and understanding the underlying mechanisms of various chemical reactions. This research can lead to the discovery of new synthetic strategies and the development of more efficient and environmentally friendly processes in the field of organic chemistry.

InChI:InChI=1/C9H10N2/c1-11-5-4-7-6-8(10)2-3-9(7)11/h2-6H,10H2,1H3

Upstream product

• 67-56-1 methanol 
• 29906-67-0 1-methyl-5-nitro-1H-indole 
• 108-98-5 thiophenol 
• 5192-03-0 5-amino-1H-indole 
• 373-68-2 tetramethylammonium fluoride 
• 865-33-8 potassium methanolate 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 6146-52-7 5-nitroindole 
• 74-88-4 methyl iodide 
• 106883-07-2 4-(1-methyl-indolin-5-ylazo)-benzenesulfonic acid 
• 108981-60-8 N-(1-methyl-indolin-5-yl)-phthalimide 
• 64180-07-0 1-methylindolin-5-amine 
• 824-21-5 N-methylindoline 
• 131013-67-7 N-(1-methyl-indol-5-yl)-phthalimide 

Downstream Products

• 412966-69-9 N-(1-methyl-indol-5-yl)-benzamide 
• 143797-63-1 N-(1-methyl-1H-indol-5-yl)-N'-3-pyridinyl-urea 
• 1146213-73-1 4-(4-fluorobenzyl)-N-(1-methyl-1H-indol-5-yl)piperazine-1-carboxamide 
• 92-52-4 biphenyl 

Relevant articles and documents

Novel anellated pyrazoloquinolin-3-ones: Synthesis and in vitro BZR activity

A series of pyrazolo[4,3-c]pyrrolo[3,2-f]quinolin-3-one derivatives 6, 7a-c, 8a,b, 9a,b and 10-12 were synthesized as modified pyrazoloquinolinone analogs (PQs) and evaluated for their ability to inhibit radioligand to central and peripheral benzodiazepin

Discovery of N-(1-(3-fluorobenzoyl)-1H-indol-5-yl)pyrazine-2-carboxamide: a novel, selective, and competitive indole-based lead inhibitor for human monoamine oxidase B

Herein, two new series of N-substituted indole-based analogues were rationally designed, synthesized via microwave heating technology, and evaluated as noteworthy MAO-B potential inhibitors. Compared to the reported indazole-based hits VI and VII, compounds 4b and 4e exhibited higher inhibitory activities over MAO-B with IC50 values of 1.65 and 0.78?μM, respectively. When compared to the modest selectivity index of rasagiline (II, a well-known MAO-B inhibitor, SI > 50), both 4b and 4e also showed better selectivity indices (SI > 60 and 120, respectively). A further kinetic evaluation of the most potent derivative (4e) displayed a competitive mode of inhibition (inhibition constant (K i)/MAO-B = 94.52 nM). Reasonable explanations of the elicited biological activities were presented via SAR study and molecular docking simulation. Accordingly, the remarkable MAO-B inhibitory activity of 4e (N-(1-(3-fluorobenzoyl)-1H-indol-5-yl)pyrazine-2-carboxamide), with its selectivity and competitive inhibition, advocates its potential role as a promising lead worthy of further optimization.

Chemoselective transfer hydrogenation of nitroarenes by highly dispersed Ni-Co BMNPs

Highly dispread Ni-Co bimetallic nanoparticles (Ni-Co BMNPs) are synthesized and applied as an efficient catalyst in the chemoselective transfer hydrogenation of nitroarenes (CTH) using hydrazine hydrate as the hydrogen donor. The BMNPs can efficiently catalyze the reduction reaction without any additives under mild conditions with high TOF. Significantly higher activity is achieved when compared with corresponding single-component catalysts, optimal composition of the Ni-Co BMNPs was screened which was proved to be crucial in both the selectivity and yields. Excellent performance of Ni-Co BMNPs can be ascribed to the improved dispersion of active sites on the BMNPs surface (compared with Ni NPs) and the electron transfer from cobalt to nickel.

Direct C-H bond arylation: Selective palladium-catalyzed C2-arylation of N-substituted indoles

(Equation Presented) We present a new, practical method by which N-substituted indoles may be selectively arylated in the C2-position with good yields, low catalyst loadings, and a high degree of functional group tolerance. Our investigation found that two competitive processes, namely, the desired cross-coupling and biphenyl formation, were operative in this reaction. A simple kinetic model was formulated that proved to be instructive and provided useful guidelines for reaction optimization; the approach described within may prove to be useful in other catalytic cross-coupling processes.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Novel heteroaryl amide derivatives as MAO-B inhibitors and pharmaceutical compositions for preventing, ameliorating or treating neurodegenerative diseases comprising the same

A novel heteroaryl amide derivative compound useful as MAO-B inhibitors. The present invention relates to a compound selected from a pharmaceutically acceptable salt thereof, a hydrate thereof, or a stereoisomer thereof, and a pharmaceutical composition comprising the compound as an active ingredient for preventing, alleviating, or treating neurodegenerative diseases such MAO as B's disease, 's disease, 's disease, and the like.

High Turnover Pd/C Catalyst for Nitro Group Reductions in Water. One-Pot Sequences and Syntheses of Pharmaceutical Intermediates

Commercially available Pd/C can be used as a catalyst for nitro group reductions with only 0.4 mol % Pd loading. The reaction can be performed using either silane as a transfer hydrogenating agent or simply a hydrogen balloon (μ1 atm pressure). With this technology, a series of nitro compounds was reduced to the desired amines in high chemical yields. Both the catalyst and surfactant were recycled several times without loss of reactivity.