125872-95-9

Basic information

• Product Name: 6-BROMO-1-METHYL-1H-INDOLE 97
• Synonyms: 6-BROMO-1-METHYL-1H-INDOLE;6-BROMO-1-METHYL-1H-INDOLE 97;6-Bromo-1-methylindole;6-Bromo-1-methylindole 97%;6-Bromo-1-methyl-1H-indole 97%;6-Bromo-1-methyl-1H-indole 95+%
• CAS NO: 125872-95-9
• Molecular Formula: C₉H₈BrN
• Molecular Weight: 210.07052
• Mol File: 125872-95-9.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 300.878 °C at 760 mmHg
• Flash Point: 135.766 °C
• Appearance: /
• Density: 1.472 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 6-BROMO-1-METHYL-1H-INDOLE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-1-METHYL-1H-INDOLE 97(125872-95-9)
• EPA Substance Registry System: 6-BROMO-1-METHYL-1H-INDOLE 97(125872-95-9)

Safety Data

• Hazard Codes: Harmful:
• Hazardous Substances Data: 125872-95-9(Hazardous Substances Data)

Usage

General Description

6-Bromo-1-methyl-1H-indole 97 is a chemical compound with a molecular formula of C9H8BrN. As implied by the name, this organic substance contains bromine and is an indole derivative, which means it has a two-ring structure of benzene and pyrrole. Its applications are broad-ranging, most commonly used in scientific research as a precursor or intermediate in the synthetic production of other complex organic compounds. As with most chemicals, safety precautions should be taken while handling, as improper exposure may pose health risks. No significant use or production of this chemical is recognized outside the pharmaceutical, polymers, plastics or related industries.

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

Upstream product

• 52415-29-9 6-bromo-1H-indole 
• 74-88-4 methyl iodide 
• 10075-50-0 5-bromo-1H-indole 
• 74-83-9 methyl bromide 
• 50-00-0 formaldehyd 

Downstream Products

• 20996-87-6 1-methyl-1H-indole-6-carbonitrile 
• 1204-32-6 methyl 1-methylindole-6-carboxylate 
• 884507-19-1 1‐methyl‐6‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐1H‐indole 
• 199589-40-7 3-(2-benzenesulfonylamino-1-benzo[1,3]dioxol-5-yl-2-oxo-ethyl)-1-methyl-1H-indole-6-carboxylic acid methyl ester 
• 199589-47-4 3-(2-benzenesulfonylamino-1-benzo[1,3]dioxol-5-yl-2-oxo-ethyl)-1-methyl-1H-indole-6-carboxylic acid 
• 199589-45-2 3-[1-benzo[1,3]dioxol-5-yl-2-oxo-2-(toluene-4-sulfonylamino)-ethyl]-1-methyl-1H-indole-6-carboxylic acid methyl ester 
• 199589-90-7 3-[1-(1,3-Benzodioxol-5-yl)-2-[(4-isopropylphenyl)sulfonamido]-2-oxoethyl]-6-cyano-1-methyl-1H-indole 
• 199589-41-8 3-[1-benzo[1,3]dioxol-5-yl-2-(4-chloro-benzenesulfonylamino)-2-oxo-ethyl]-1-methyl-1H-indole-6-carboxylic acid methyl ester 
• 199589-48-5 3-[1-benzo[1,3]dioxol-5-yl-2-(4-chloro-benzenesulfonylamino)-2-oxo-ethyl]-1-methyl-1H-indole-6-carboxylic acid 
• 199589-52-1 3-[1-benzo[1,3]dioxol-5-yl-2-oxo-2-(toluene-4-sulfonylamino)-ethyl]-1-methyl-1H-indole-6-carboxylic acid 

Relevant articles and documents

Electronic Nature of Ketone Directing Group as a Key to Control C-2 vs C-4 Alkenylation of Indoles

A novel mode of achieving site selectivity between C-2 and C-4 positions in the indole framework by altering the property of the ketone directing group is disclosed. Methyl ketone, as directing group, furnishes exclusively C-2 alkenylated product, whereas trifluoromethyl ketone changes the selectivity to C-4, indicating that the electronic nature of the directing group controls the unusual choice between a 5-membered and a 6-membered metallacycle. The screening of other carbonyl-derived directing groups reveals that strong and weak directing groups exhibit opposite selectivity. Experimental controls and deuteration experiments lend support to the proposed mechanism.

Catalytic generation of borenium ions by cooperative B-H bond activation: The elusive direct electrophilic borylation of nitrogen heterocycles with pinacolborane

The B-H bond of typical boranes is heterolytically split by the polar Ru-S bond of a tethered ruthenium(II) thiolate complex, affording a ruthenium(II) hydride and borenium ions with a dative interaction with the sulfur atom. These stable adducts were spectroscopically characterized, and in one case, the B-H bond activation step was crystallographically verified, a snapshot of the σ-bond metathesis. The borenium ions derived from 9-borabicyclo[3.3.1] nonane dimer [(9-BBN)2], pinacolborane (pinBH), and catecholborane (catBH) allowed for electrophilic aromatic substitution of indoles. The unprecedented electrophilic borylation with the pinB cation was further elaborated for various nitrogen heterocycles.

Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position

Herein, Rh(III)-catalyzed C4-selective C?H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished. (Figure presented.).

Silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof

The invention discloses a silicon-based rhodamine fluorescent staining reagent as well as a preparation method and application thereof, and belongs to the field of organic chemistry and biochemistry.According to the silicon-based rhodamine fluorescent staining reagent as well as preparation method and application thereof of the invention, a silicon atom substituted rhodamine derivative is used asa basic frame, and is modified with aromatic amines in different forms, so that the silicon-based rhodamine fluorescent staining reagent which has large Stokes shift and high fluorescence intensity and can mark immunoglobulin IgG can be synthesized, so that the silicon-based rhodamine fluorescent staining reagent can be used for in-vitro SARS-CoV2-virus specific antibody fluorescence ELISA detection. The silicon-based rhodamine fluorescence staining reagent has large Stokes shift (greater than 140 nm), can effectively avoid mutual interference of excitation light and emitted light, and is high in detection sensitivity; a fluorescence ELISA detection method established based on the fluorescence antibody can be suitable for microplate readers with different bandwidths, and is wide in application range.

Tandem iridium-catalyzed decarbonylative c-h activation of indole: Sacrificial electron-rich ketone-assisted bis-arylsulfenylation

Described herein is a decarbonylative tandem C-H bis-arylsulfenylation of indole at the C2 and C4 C-H bonds through the use of pentamethylcyclopentadienyl iridium dichloride dimer ([Cp?IrCl2]2) catalyst and disulfides. A new sacrificial electron-rich adamantoyl-directing group facilitates indole C-H bis-functionalization with a traceless in situ removal. Various differently substituted disulfides can be easily accommodated in this reaction by a coordination to Ir(III) through the formation of six- and five-membered iridacycles at the C2 and C4 positions, respectively. Mechanistic studies show that a C-H activation-induced C-C activation is involved in the catalytic cycle.