4671-26-5

Usage

Uses

Used in Fragrance Industry:
2,5-dimethyl-3-phenyl-1H-indole is used as a fragrance ingredient in perfumes for its unique scent, enhancing the overall aroma and appeal of the product.
Used in Food Industry:
In the food industry, 2,5-dimethyl-3-phenyl-1H-indole serves as a flavoring agent, particularly in the production of chocolate, where it contributes to the characteristic taste and aroma.
Used in Pharmaceutical Research:
2,5-dimethyl-3-phenyl-1H-indole is used as a subject of research for its potential medicinal properties, exploring its use in treating certain neurological and psychological disorders.
However, it is crucial to handle 2,5-dimethyl-3-phenyl-1H-indole with care due to its potential toxicity in high concentrations.

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 99-99-0 1-methyl-4-nitrobenzene 
• 106-49-0 p-toluidine 
• 4436-22-0 1-phenylpropylene oxide 
• 1196-79-8 2,5-Dimethyl-1H-indole 
• 591-50-4 iodobenzene 
• 583-68-6 2-bromo-p-toluidine 

Relevant academic research and scientific papers

Transition-Metal-Free C3 Arylation of Indoles with Aryl Halides

We report an unprecedented transition metal-free coupling of indoles with aryl halides. The reaction is promoted by KOtBu and is regioselective for C3 over N. The use of degassed solvents devoid of oxygen is necessary for the success of the transformation. Preliminary studies implicate a hybrid mechanism that involves both aryne intermediates and non-propagative radical processes. Electron transfer is also a distinct possibility. These conclusions were substantiated by EPR data, isotopic labeling studies, and the use of radical scavengers and electron transfer inhibitors.

Ruthenium-catalyzed synthesis of indoles from anilines and epoxides

A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru3(CO)12]/1,1-bis(diphenylphosphino)ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by-products, making this process highly atom efficient.

The regioselective Larock indole synthesis catalyzed by NHC-palladium complexes

The first practical and regioselective process for the synthesis of 2,3-disubstituted indoles from the reaction of o-iodoanilines or o-bromoanilines and their derivatives with symmetrical and unsymmetrical internal alkynes catalyzed by a ferrocene-functionalized N-heterocyclic carbene (NHC)-palladium complex has been developed, and the indoles were isolated in good yields with high regioselectivity.

Regioselective Pd-catalyzed indolization of 2-bromoanilines with internal alkynes using phosphine-free ligands

The possibility of using phosphine-free ligands to promote Pd-catalyzed indolization of 2-bromoanilines with internal alkynes was examined for the first time. Phenylurea was found to be the optimal ligand, which could mediate the synthesis of 2,3-disubsti

Synthesis of indoles by intermolecular cyclization of unfunctionalized nitroarenes and alkynes, catalyzed by palladium-phenanthroline complexes

Palladium-phenanthroline complexes efficiently catalyze the reaction of nitroarenes with arylalkynes and CO to give 3-arylindoles by an ortho-C-H functionalization of the nitroarene ring. Both electron-withdrawing and electron-donating substituents are tolerated on the nitroarene, except for bromide and activated chloride. Nitroarenes bearing electron-withdrawing substituents react faster, but the selectivity of the reaction depends on both polar and radical stabilization effects. Among those tested, only arylalkynes afforded indoles under the investigated conditions. The reaction mechanism was partly investigated. The kinetics is first order in nitroarene concentration and the rate-determing step of the cycle is the initial nitroarene reduction. No primary isotope effect is observed on either rate or selectivity, implying that the cyclization step is fast.