1075-34-9

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-methylindole is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting neurological and psychiatric disorders.
Used in Chemical Research:
In the field of chemical research, 5-Bromo-2-methylindole serves as a valuable compound for studying the properties and reactivity of bromoalkylindole derivatives. It can be used to explore new reaction pathways and develop innovative synthetic methods.
Used in Material Science:
5-Bromo-2-methylindole can be utilized as a building block for the development of novel materials with specific properties, such as optoelectronic materials or advanced polymers. Its unique structure may contribute to the creation of materials with enhanced performance characteristics.
Used in Analytical Chemistry:
As a compound with distinct spectroscopic features, 5-Bromo-2-methylindole can be employed as a reference material or standard in analytical chemistry. It can be used to calibrate instruments, validate analytical methods, or as an internal standard in quantitative analyses.
Used in Environmental Science:
5-Bromo-2-methylindole may also find applications in environmental science, particularly in the development of new methods for the detection and monitoring of pollutants or contaminants. Its unique chemical properties could be harnessed to create sensitive and selective sensors for environmental monitoring.

InChI:InChI=1/C9H8BrN/c1-6-4-7-5-8(10)2-3-9(7)11-6/h2-5,11H,1H3

Upstream product

• 67-64-1 acetone 
• 589-21-9 (4-bromophenyl)hydrazine 
• 13061-96-6 dihydroxy-methyl-borane 
• 1240045-42-4 2,5-dibromo-1H-indole 
• 95-20-5 2-methyl-1H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 74-83-9 methyl bromide 
• 20357-20-4 5-bromo-2-nitrobenzaldehyde 
• 56904-86-0 tert-butyl 2-(triphenylphosphoranylidene)propionate 
• 267002-57-3 2-allyl-4-bromoaniline 
• 106-40-1 4-bromo-aniline 
• 6872-06-6 2-methyl indoline 
• 158585-48-9 5-bromo-2-methyl-3-(phenylthio)-1H-indole 
• 99847-70-8 5-bromo-2-methyl-2,3-dihydroindole 

Downstream Products

• 99847-70-8 5-bromo-2-methyl-2,3-dihydroindole 
• 181299-26-3 1-benzenesulfonyl-5-bromo-2-methyl-1H-indole 
• 236747-79-8 methyl 2-[4-(2-methyl-1H-5-indolyl)phenyl]propanoate 
• 72016-68-3 5-bromo-2-methyl-1H-indole-3-acetic acid ethyl ester 
• 919295-67-3 5-bromo-2-methyl-1-(phenylsulfonyl)-1H-indole-3-carbaldehyde 
• 919295-68-4 (1-benzenesulfonyl-5-bromo-2-methyl-1H-indol-3-yl)-methanol 
• 919295-70-8 N-(1-benzenesulfonyl-5-bromo-2-methyl-1H-indol-3-ylmethyl)-hydroxylamine 
• 919295-69-5 tert-butyl (5-bromo-2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl)methyl(tert-butoxycarbonyloxy)carbamate 
• 837392-54-8 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 1122006-91-0 (-)-7-bromo-3a-methyl-1-phenyl-4,8b-dihydro-3aH-cyclopenta[b]-indol-3-one 
• 1122006-95-4 (+)-7-bromo-1-(4-chloro-phenyl)-3a-methyl-4,8b-dihydro-3aH-cyclopenta[b]-indol-3-one 
• 1219741-76-0 methyl 5-[(6-chloro-5-(2-methyl-1H-indol-5-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate 
• 1227380-58-6 C₁₇H₁₅BrN₂O₂ 
• 4583-55-5 5-bromo-2,3-dimethyl-1H-indole 

Relevant academic research and scientific papers

Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents

The selective oxidation of C2-alkyl-substituted indoles to 3-oxindole and the selective C-H oxygenation or amination of C2,C3-dialkyl-substituted indoles at C2 are reported under mild conditions. The position of the alkyl substitution on the indole directs the reaction to different pathways under similar conditions.

Tandem Wittig – Reductive annulation decarboxylation approach for the synthesis of indole and 2-substituted indoles

A simple tandem Wittig reaction-reductive decarboxylation route is established for the synthesis of indoles from commercially available o-nitrobenzaldehydes and a stable phosphorane. The method allows access to indoles in a very fast manner without involving any metal or expensive reagents or inert atmosphere. Also 2-substituted indoles are obtained which forms an important core of many biological active compounds.

Asymmetric Hydrogenation of Unprotected Indoles Catalyzed by η6-Arene/N-Me-sulfonyldiamine-Ru(II) Complexes

Protecting-group-free transformation is a challenging and important issue in atom-economical organic synthesis. The η6-arene/N-Me-sulfonyldiamine-Ru(II)-BF4 complex-catalyzed asymmetric hydrogenation of 2-substituted unprotected indoles in weakly acidic hexafluoroisopropanol gives optically active indoline compounds with up to >99% ee. Under mild reaction media, halogen atoms and synthetically important protecting groups (e.g., silyl ether, acetal, benzyl ether, and ester) on indoles are maintained, which is advantageous for the synthesis of further complex indoline molecules.

A N-heterocyclic carbene (NHC) platinum complex as pre-catalyst for the intramolecular hydroamination of olefins with secondary alkylamines and oxidative amination of ω-alkenic amines

A N-heterocyclic carbene (NHC) platinum complex 3 prepared from BINAM was found to be a highly effective pre-catalyst for the intramolecular hydroamination of olefins with secondary alkylamines to give the corresponding intramolecular hydroamination products in excellent yields. The substrate scope has been carefully examined and the plausible reaction mechanism has been also proposed.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: Hit to lead studies

A series of benzofuran-3-one indole phosphatidylinositol-3-kinases (PI3K) inhibitors identified via HTS has been prepared. The optimized inhibitors possess single digit nanomolar activity against p110α (PI3K-α), good pharmaceutical properties, selectivity versus p110γ (PI3K-γ), and tunable selectivity versus the mammalian target of rapamycin (mTOR). Modeling of compounds 9 and 32 in homology models of PI3K-α and mTOR supports the proposed rationale for selectivity. Compounds show activity in multiple cellular proliferation assays with signaling through the PI3K pathway confirmed via phospho-Akt inhibition in PC-3 cells.

Unusual acetylation of 2-methyl-1-phenylsulfonylindole

Acetylation of 2-methyl-1-phenylsulfonylindole with an excess of aluminium chloride and acetic anhydride afforded exclusively 6-acetyl-3-chloro-2-methylindole and 6-acetyl-3-chloro-2-methyl-1-phenylsulfonylindole.

Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction.We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring.In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched.Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides.This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.