824-21-5

Usage

Uses

Used in Pharmaceutical Industry:
1-Methylindoline is used as an intermediate in the production of various pharmaceuticals for its role in the synthesis of indole compounds, which exhibit diverse biological activities such as anti-inflammatory, antimicrobial, and anti-cancer properties.
Used in Dye and Perfume Industry:
1-Methylindoline is used as a key component in the formulation of dyes and perfumes, leveraging its unique chemical properties to create a variety of colorants and fragrances.
Used in Organic Synthesis:
1-Methylindoline is used as a building block in the synthesis of various organic compounds, contributing to the development of new chemical entities with potential applications in various fields.
Used in Electronic Devices:
1-Methylindoline is studied for its potential as an organic semiconductor, which could be utilized in the development of electronic devices, taking advantage of its electronic properties for improved performance and functionality.

InChI:InChI=1/C9H11N/c1-10-7-6-8-4-2-3-5-9(8)10/h2-5H,6-7H2,1H3

Upstream product

• 61-70-1 N-methyl-2-indolinone 
• 52516-20-8 2-(3-Chlorophenyl)-N-methylethan-1-amine 
• 52516-17-3 2-(2-chlorochlorophenyl)-N-methylethanamine 
• 591-51-5 phenyllithium 
• 120-72-9 indole 
• 64-18-6 formic acid 
• 603-76-9 1-methylindole 
• 60-29-7 diethyl ether 
• 103200-09-5 phenyl 2-(N,N-dimethylamino)benzyl ether 
• 1361538-03-5 N-(2-(dimethylamino)benzylidene)-2-phenylaziridin-1-amine 
• 579-72-6 2-(dimethylamino)benzaldehyde 
• 789-25-3 HSiPh₃ 
• 694-53-1 phenylsilane 
• 776-76-1 methyldiphenylsilane 

Downstream Products

• 871883-25-9 [2-(2-dimethylamino-ethyl)-phenyl]-methyl-carbamonitrile 
• 115210-53-2 1-methyl-6-nitroindoline 
• 94258-40-9 4-(1-methyl-2,3-dihydro-indol-5-ylmethylene)-2-phenyl-4H-oxazol-5-one 
• 74023-54-4 Methyl-[2-(2-phenylselanyl-ethyl)-phenyl]-amine 
• 76108-10-6 1-amino-1-methylindolinium mesitylenesulfonate 
• 660-68-4 diethyl amine hydrochloride 
• 83595-34-0 5--1-methylindoline 
• 603-76-9 1-methylindole 
• 60082-02-2 1-methylindoline-5-carboxaldehyde 
• 496-15-1 1-indoline 
• 106883-07-2 4-(1-methyl-indolin-5-ylazo)-benzenesulfonic acid 
• 101-99-5 N-carboethoxyaniline 
• 102-07-8 bis(diphenyl)urea 
• 10075-52-2 5-bromo-1-methyl-H-indole 

Relevant academic research and scientific papers

Application of Mutualism in Organic Synthetic Chemistry: Mutually Promoted C?H Functionalization of Indole and Reduction of Quinoline

Here we reported a one-pot, metal-free B(C6F5)3-catalyzed strategy for simultaneous synthesis of C3-regioselective functionalization of indoles and complete reduction of quinolines. It turned out that by sharing a quinolinium hydridoborate intermediate, the original determining steps with high energy barrier in both the convergent disproportionation of indole and reduction of quinoline could be realized at room temperature, thus furnishing both the C3-borylated (or silylated) indoles and N-borylated tetrahydroquinolines in up to 98% yields at room temperature. Mechanistic studies suggested that both reactions would consume a product generated from the other reaction such that they can mutually promote each other, thus producing desirable products in a high atom-economy and low energy-cost manner. This strategy opened the gate to introducing mutualism to the field of chemistry. (Figure presented.).

Catalytic system for efficiently catalyzing indole silanization and proton transfer hydrogenation

The invention discloses a catalytic system for efficiently catalyzing indole silanization and proton transfer hydrogenation, and belongs to the technical field of organic synthesis. According to the catalytic system, indole and silane serve as raw materials, tris(pentafluorophenyl) boron (B (C6F5)3) serves as a catalyst, reaction is performed for 10 minutes at the indoor temperature to simultaneously achieve 3-position selective indole silanization and proton transfer hydrogenation or reaction is performed for 10-1440 minutes at the temperature ranging from 100 DEG C to 140 DEG C to achieve 3-position efficient and specific catalytic indole silanization. The catalytic system has the advantages that the catalytic system is convenient to operate, mild in reaction condition, rapid in reaction, high in conversion rate, less in catalyst consumption and applicable to various solvent systems or body systems without any solvents, raw materials are easily acquired, precious metal is omitted, a catalytic intermediate is high in stability and the like.

B(C6F5)3-Catalyzed (Convergent) Disproportionation Reaction of Indoles

A metal-free B(C6F5)3-catalyzed approach is developed for the disproportionation reaction of a series of indoles with various hydrosilanes, without any additives such as base and production of any small molecule such as dihydrogen. This boron catalyst system also exhibits excellent catalytic performance for practical application, such as catalyst loading as low as 0.01 mol % under solvent-free conditions, and a long-life catalytic performance highlighted by a constant catalytic activity being maintained and excellent yields being achieved for the desired products over 10 sequential additions of starting materials. On the basis of characterization of key intermediates through a series of in situ NMR reactions and detailed experimental data, we proposed a reaction mechanism which illustrated pathways for the formation of different products, including both major products and byproducts. Additional control experiments were conducted to support our proposed mechanism. Understanding the mechanism enables us to successfully suppress side reactions by choosing appropriate substrates and hydrosilanes. More importantly, the use of an elevated reaction temperature for continuous oxidation of the resulting indoline to indole makes the convergent disproportionation reaction an ideal atom-economical process. Near-quantitative conversions and up to 99% yields of C3-silylated indoles were achieved for various indoles with trisubstituted silanes, Ph3SiH (2b) or Ph2MeSiH (2d).

Br?nsted acid-promoted formation of stabilized silylium ions for catalytic friedel-crafts C-H silylation

A counterintuitive approach to electrophilic aromatic substitution with silicon electrophiles is disclosed. A strong Br?nsted acid that would usually promote the reverse reaction, i.e., protodesilylation, was found to initiate the C-H silylation of electron-rich (hetero)arenes with hydrosilanes. Protonation of the hydrosilane followed by liberation of dihydrogen is key to success, fulfilling two purposes: to generate the stabilized silylium ion and to remove the proton released from the Wheland intermediate.

N-fused indolines through non-carbonyl-stabilized rhodium carbenoid C-H insertion of N-aziridinyl imines

Under rhodium catalysis, N-aziridinyl imines provided access to N-fused indolines through non-carbonyl-stabilized rhodium carbenoid C-H insertion. The utility of this methodology for the synthesis of architecturally complex heterocycles was further demonstrated by an expedient total synthesis of ( ±)-cryptaustoline (see scheme). Copyright

154. Reduction of Indolin-2-ones and Desulfurization of Indoline-2-thiones to Indoline and Indole Derivatives

Reduction of indolin-2-ones with lithium aluminium hydride (LAH) or diisobutylaluminium hydride (DIBAL) and desulfurization of indoline-2-thiones with Raney-Ni were investigated.Treatment of indolin-2-ones 1 with LAH or DIBAL yielded indoles 4 and/or indolines 3 in moderate-to-high yields depending on the substituents at N and C(3) of 1.Indoline-2-thiones 2 were desulfurized with Raney-Ni tigive indoles 4 and/or indolines 3.

Gas Phase Generation and Reactions of o-Dialkylaminobenyzl and o-Dialkylaminophenoxyl Radicals

Generation of the title radicals was effected by flash vacuum pyrolysis of benzyl phenyl ethers, and O-allyl ethers, respectively.The major products are formed by a multi-step sequence involving (i) intramolecular hydrogen transfer from the alkylamino group to the initial radical cemtre, (ii) rearrangement of the resulting aminoalkyl radical, (iii) expulsion of the nitrogen residue to give a bezyl radical which leads to products.

Electroreduction of Bicyclic Heteroaromatics. Selective Product Formation

The electroreductions of 1-methylindole and several benzofurans were investigated and compared with the corresponding alkali-metal/liquid ammonia reductions.The cathodic reductions were performed using a simple apparatus with aqueous THF as the solvent and were found to be regioselective.Over-reduction and other side reactions were avoided.The possible mechanism of the electroreductions is discussed.

ON THE REACTION OF INDOLE WITH SODIUM BOROHYDRIDE IN FORMIC ACID

The reaction of indole (1) with sodium borohydride in formic acid yields N-methylindoline (3) and a product derived from "indole dimer", 3-(2-(N,N-dimethylaminophenyl)ethyl)-1-methylindoline (4), whose structure is proved by independent synthesis.