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Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2,3-dihydro-1H-indole is utilized as a key intermediate in the synthesis of pharmaceutical drugs due to its ability to be incorporated into various biologically active molecules. Its presence in the molecular structure can modulate the pharmacological activity of the resulting compounds, making it a valuable asset in drug development.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Bromo-2,3-dihydro-1H-indole serves as a precursor for the development of agrochemicals, where its unique structural features can be leveraged to create molecules with specific pesticidal or herbicidal properties, contributing to more effective crop protection strategies.
Used in Organic Synthesis:
4-Bromo-2,3-dihydro-1H-indole is employed as a building block in organic synthesis for the creation of complex organic molecules. Its reactivity and structural characteristics facilitate the formation of diverse chemical entities, which can be applied across various scientific and industrial fields.
Used in Medicinal Chemistry Research:
As a compound with potential pharmacological properties, 4-Bromo-2,3-dihydro-1H-indole is used in medicinal chemistry research to explore its role as a serotonin receptor agonist, antihypertensive agent, and its anti-cancer potential. This research can lead to the discovery of new therapeutic agents and a deeper understanding of molecular interactions within biological systems.

Upstream product

• 496-15-1 1-indoline 
• 52488-36-5 4-bromo-1H-indole 
• 120-72-9 indole 
• 99365-48-7 4-bromoindolin-2-one 

Downstream Products

• 1160359-95-4 4-bromo-1-(4-fluorobenzyl)indoline 
• 937591-97-4 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-1-yl)ethanone 
• 1622173-47-0 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline 
• 20780-72-7 4-bromoisatin 
• 52488-36-5 4-bromo-1H-indole 
• 179473-53-1 4-phenyl-2,3-dihydro-1H-indole 
• 885278-80-8 indoline-4-carbonitrile 
• 1578263-74-7 C₁₉H₁₆BrFN₂O₃ 
• 1578263-73-6 C₁₉H₁₆Cl₂N₂O₃ 
• 1578263-72-5 C₁₉H₁₆ClFN₂O₃ 
• 1578263-71-4 C₂₀H₁₉ClN₂O₄ 
• 1578263-70-3 C₂₀H₁₉FN₂O₄ 
• 1578263-69-0 C₂₀H₁₉ClN₂O₄ 
• 1578263-68-9 C₂₁H₁₉N₃O₄ 

Relevant academic research and scientific papers

Concerning the preparation of 6-bromotryptamine

Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.

Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations

Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

A Diels–Alder reaction-based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne-tethered 3-aminopyrones gives 4-substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non-canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.

640nm excited near-infrared fluorescent dye and preparation method thereof

The invention provides 640nm excited near-infrared fluorescent dye and a preparation method thereof. The structure of the dye is modified by nitrogen ends of a five-membered ring and a six-membered ring with different rigidities, the dye is specifically shown as a formula (1), absorption and red shift of a fluorescence spectrum are realized, and the maximum red shift is 45 nm. Meanwhile, the dye provided by the invention is high in light stability and high in quantum yield (reaching 0.3 or above in methanol), the spiral ring opening and closing forms of a bottom ring of the dye respectively correspond to colourlessness and colorless, light regulation and control can be carried out, and the dye is used for a biological fluorescent probe and super-resolution imaging of the biological fluorescent probe.

Hydrogenation or Dehydrogenation of N-Containing Heterocycles Catalyzed by a Single Manganese Complex

A highly chemoselective base-metal catalyzed hydrogenation and acceptorless dehydrogenation of N-heterocycles is presented. A well-defined Mn complex operates at low catalyst loading (as low as 2 mol %) and under mild reaction conditions. The described catalytic system tolerates various functional groups, and the corresponding reduced heterocycles can be obtained in high yields. Experimental studies indicate a metal-ligand cooperative catalysis mechanism.

Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines

Tandem C-N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.

Indoline compounds used as immunomodulator, and preparation method thereof

The invention relates to the technical field of medicines, and relates to indoline compounds used as an immunomodulator, stereoisomers and pharmaceutically acceptable salts thereof, a preparation method thereof, and a medicinal composition containing the

Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles

We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

Ru(ii)-Catalyzed C7-acyloxylation of indolines with carboxylic acids

Ruthenium(ii)-catalyzed site-selective C7-acyloxylation of indolines with carboxylic acids is presented. The substrate scope and functional group tolerance are important practical features. The kinetic isotope studies suggest that C-H bond activation may be the rate-determining step.

Expedient cobalt(II)-catalyzed site-selective C7-arylation of indolines with arylboronic acids

Cobalt(ii)-catalyzed pyrimidyl directing group-assisted C7 arylation of indolines with arylboronic acids has been developed using Mn(OAc)2·4H2O as an oxidant. The use of cobalt(ii)-PCy3 as a catalyst and broad substrate scope are the important practical features.