10075-52-2

Basic information

• Product Name: 5-Bromo-1-methyl-1H-indole
• Synonyms: CHEMBRDG-BB 9072049;5-BROMO-1-METHYL-INDOLE;5-BROMO-1-METHYL-1H-INDOLE;5-Bromo-1-methy-1H-indole;5-bromo-1-methyl-1H-indole(SALTDATA: FREE);1-methyl-5-bromoindole;N-Methyl-5-bromoindole;5-Bromo-1-methylindole 97%
• CAS NO: 10075-52-2
• Molecular Formula: C₉H₈BrN
• Molecular Weight: 210.07
• Product Categories: blocks;Bromides;IndolesOxindoles;Indole
• Mol File: 10075-52-2.mol

Chemical Properties

• Melting Point: 43 °C
• Boiling Point: 300.9 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 0.00195mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-Bromo-1-methyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1-methyl-1H-indole(10075-52-2)
• EPA Substance Registry System: 5-Bromo-1-methyl-1H-indole(10075-52-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38-41-37/38
• Safety Statements: 22-26-36/37/39-39
• WGK Germany: 3
• Hazardous Substances Data: 10075-52-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-1-methyl-1H-indole is used as a key intermediate for the synthesis of indole-based compounds, which are crucial in the production of various drugs. It plays a significant role in the development of antipsychotics, antihypertensives, and anti-infectives, contributing to the advancement of medical treatments.
Used in Organic Synthesis:
In the field of organic chemistry, 5-Bromo-1-methyl-1H-indole is utilized as a reagent to introduce the 5-bromine substituent into various molecules. This property allows for the creation of new compounds with specific functionalities and properties, expanding the scope of chemical research and development.
Used in Agrochemical Industry:
5-Bromo-1-methyl-1H-indole is also employed in the agrochemical sector, where it serves as a building block for the synthesis of various agrochemicals. Its use in this industry contributes to the development of effective and targeted solutions for agricultural challenges, such as pest control and crop protection.

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

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 865-33-8 potassium methanolate 
• 96546-77-9 N-tosyl-5-bromoindole 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 74-83-9 methyl bromide 
• 120-72-9 indole 
• 25055-55-4 2,3,5,6-tetrabromo-1-methyl-1H-indole 
• 603-76-9 1-methylindole 
• 1352622-04-8 1-bromo-2-[(4-bromophenyl)methylamino]ethanesulfonic acid 2,4,6-trichlorophenyl ester 
• 1352621-93-2 1-bromo-2-(4-bromophenylamino)ethanesulfonic acid 2,4,6-trichlorophenyl ester 
• 74-88-4 methyl iodide 
• 80-48-8 methyl p-toluene sulfonate 
• 616-38-6 carbonic acid dimethyl ester 
• 106883-07-2 4-(1-methyl-indolin-5-ylazo)-benzenesulfonic acid 

Downstream Products

• 1392298-23-5 methyl 2-(5-bromo-1-methyl-1H-indol-3-yl)-2-phenylacetate 
• 1646144-86-6 ethyl 2-(5-bromo-1-methyl-1H-indol-3-yl)-2-phenylacetate 
• 1427690-74-1 C₂₀H₁₉NO₅ 
• 1427690-73-0 1-methyl-5-(3,4,5-trimethoxybenzoyl)-1H-indole-3-carbaldehyde 
• 1192108-54-5 1-methyl-5-[1-(2,3,4-trimethoxyphenyl)vinyl]-1H-indole 
• 1192108-55-6 1-methyl-5-[1-(3,4,5-trimethoxyphenyl)vinyl]-1H-indole 
• 1192108-48-7 C₁₉H₁₉NO₄ 
• 946077-08-3 (1-methyl-1H-indol-5-yl)-(3,4,5-trimethoxyphenyl)-methanone 
• 1427690-95-6 C₂₁H₂₃NO₄ 
• 1427690-94-5 C₂₁H₂₃NO₄ 
• 1427690-93-4 C₂₁H₂₂N₂O₄ 
• 1427690-90-1 C₂₁H₂₀N₂O₃ 
• 1427690-88-7 C₂₁H₂₀N₂O₃ 
• 1427690-89-8 1-methyl-5-[1-(3,4,5-trimethoxyphenyl)vinyl]-1H-indole-3-carbaldehydeoxime acetate 

Relevant articles and documents

Selective Methylation of Amides, N-Heterocycles, Thiols, and Alcohols with Tetramethylammonium Fluoride

We herein disclose the use of tetramethylammonium fluoride (TMAF) as a direct and selective methylating agent of a variety of amides, indoles, pyrroles, imidazoles, alcohols, and thiols. The method is characterized by operational simplicity, wide scope, and ease of purification. Our computational studies suggest a concerted methylation-deprotonation as the preferred reaction pathway.

Straightforward access to novel indolo[2,3-: B] indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles

Herein, we report an unprecedented aerobic copper-catalyzed [3+2] annulation reaction of diarylamines with indoles, which allows direct access to novel 2-diarylaminoindolo[2,3-b]indoles, a class of potential photoelectric device molecules. The developed transformation proceeds with broad substrate scope, good functional group tolerance, high chemo-selectivity, and no need for pre-preparation of specific agents, which offers a practical route for diverse and atom-economic synthesis of the desired products that are difficult to prepare with the conventional approaches.

Convenient synthesis of 1H-indol-1-yl boronates via palladium(0)-catalyzed borylation of bromo-1H-indoles with 'pinacolborane'

An atom-economic Pd0-catalyzed synthesis of a series of pinacol-type indolylboronates 3 from the corresponding bromoindole substrates 2 and pinacolborane (pinBH) as borylating agent was elaborated. The optimal catalyst system consisted of a 1:2 mixture of [Pd(OAc)2] and the ortho-substituted biphenylphosphine ligand L-3 (Scheme 4, Table). Our synthetic protocol was applied to the fast, preparative-scale synthesis of 1-substituted indolylboronates 3a-h in the presence of different functional groups, and at a catalyst load of only 1 mol-% of Pd.

Synthesis of Cyclopenta[b]indoles via a Formal [3+2] Cyclization of N-Sulfonyl-1,2,3-triazoles and Indoles

Annulation of benzoxy-tethered N-sulfonyl-1,2,3-triazoles and indoles has been developed in this paper, providing an efficient and convenient access to valuable cyclopenta[b]indoles in moderate to good yields. α,β-Unsaturated imine, which generated in situ from denitrogenation and 1,2-OBz migration of triazole, provided three carbons for the formal [3+2] cyclization reaction for the first time. (Figure presented.).

Synthesis, biological evaluation, and molecular docking analysis of phenstatin based indole linked chalcones as anticancer agents and tubulin polymerization inhibitors

A library of new phenstatin based indole linked chalcone compounds (9a-z and 9aa-ad) were designed and synthesized. Of these, compound 9a with 1-methyl, 2- and 3-methoxy substituents in the aromatic ring was efficacious against the human oral cancer cell

Assembly of polycyclic N-heterocycles: Via copper-catalyzed cycloamination of indolylquinones and aromatic amines

The copper-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amines under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. This method allows facile access to polycyclic N-heterocycles with the tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (60-89%).

Copper-mediated rapid and facile oxidative dehydrogenation of dihydrobenzocarbazoles

Rapid method for the oxidative dehydrogenation of dihydrobenzocarbazoles has been introduced by using bench scale and commercially available reagent; copper chloride, in excellent yield with easy workup. The scope of the reaction has been studied with broad range of substitutes.

Trichloromethylthiolation of N-Heterocycles: Practical and Completely Regioselective

The first trichloromethylthiolation of a broad range of indoles and pyrroles is reported employing bench-stable N-trichloromethylthiosaccharin as reagent. This methodology is highly regioselective, exhibits high functional group tolerance, and provides access to two previously unknown classes of potentially bioactive compounds.

Cobalt-Catalyzed Cycloamination: Synthesis and Photophysical Properties of Polycyclic N-Heterocycles

The first earth-abundant cobalt-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amine under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. The process allows facile access to polycyclic N-heterocycles with tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (up to 89percent). In addition, The photophysical properties of the synthesized products were evaluated. These products exhibit interesting fluorescence properties, which is promising for fluorescent probes.

Dual nucleophilic catalysis with DABCO for the N-methylation of indoles

DABCO is an extremely active catalyst for the methylation of indoles in conjunction with dimethyl carbonate (DMC). This green chemistry is highly effective and produces N-methylindoles in nearly quantitative yields. The reaction sequence consists of competing alkylation and acylation pathways and involves 1,4-diazabicyclo[2.2.2]octane (DABCO) dually as a nucleophilic catalyst, ultimately resulting in a single product: the N-methylated indole.