85092-83-7

Basic information

• Product Name: 1H-INDOLE, 3-BROMO-5-METHOXY-
• Synonyms: 1H-INDOLE, 3-BROMO-5-METHOXY-;3-Bromo-5-methoxyindole;3-BROMO-5-METHOXY-1H-INDOLE
• CAS NO: 85092-83-7
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.07
• Product Categories: Indole
• Mol File: 85092-83-7.mol

Chemical Properties

• Boiling Point: 355.6 °C at 760 mmHg
• Flash Point: 168.9 °C
• Appearance: /
• Density: 1.591 g/cm³
• Vapor Pressure: 6.34E-05mmHg at 25°C
• Refractive Index: 1.667
• PKA: 15.04±0.30(Predicted)
• CAS DataBase Reference: 1H-INDOLE, 3-BROMO-5-METHOXY-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE, 3-BROMO-5-METHOXY-(85092-83-7)
• EPA Substance Registry System: 1H-INDOLE, 3-BROMO-5-METHOXY-(85092-83-7)

Safety Data

• Hazardous Substances Data: 85092-83-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole, 3-bromo-5-methoxyis used as a building block in the synthesis of various organic compounds for pharmaceutical applications. Its unique structure and functional groups make it a valuable component in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, 1H-Indole, 3-bromo-5-methoxyis utilized as a precursor or intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its biological activity and chemical properties contribute to the effectiveness of these products.
Used in Material Science:
1H-Indole, 3-bromo-5-methoxyalso finds applications in material science, where it can be used to develop new materials with specific properties. Its chemical structure and reactivity make it a promising candidate for the synthesis of advanced materials with potential applications in various industries.
Used in Research and Development:
As a chemical compound with unique properties, 1H-Indole, 3-bromo-5-methoxyis commonly used in research and development for the exploration of new chemical reactions, synthesis methods, and potential applications. Its versatility and reactivity make it an essential tool for scientists and researchers in various fields.

InChI:InChI=1/C9H8BrNO/c1-12-6-2-3-9-7(4-6)8(10)5-11-9/h2-5,11H,1H3

Upstream product

• 1006-94-6 5-methoxylindole 

Relevant articles and documents

Synthesis and anti-tumor activity of marine alkaloids

Marine alkaloids were divided into five categories from the perspective of anti-tumor activity. The optimization process, chemical synthesis, anti-tumor activity evaluation and structure–activity relationship of various compounds were discussed.

PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives

This paper describes a mild phenyliodine diacetate mediated method for selective chlorination, bromination, and iodination of indole C-H bonds using sodium halide as a source for analogous halogenations. The combination of NaX and phenyliodine diacetate provides an invincible system for halogenation of indoles. This protocol was compatible with a wide array of indole substrates and provides straight forward access to potential halogenated arenes.

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The human antigen R (HuR) is an RNA-binding protein known to modulate the expression of target mRNA coding for proteins involved in inflammation, tumorigenesis, and stress responses and is a valuable drug target. We previously found that dihydrotanshinone

AZA-TANSHINONE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE IN THERAPY

Object of the present invention are new aza-tanshinone derivatives, a method for their preparation and their use in therapy, particularly, but not limited to, as anti? tumor agents and anti-inflammatories. The invention comprises also the pharmaceutical c

Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin

Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.

Synthesis and biological evaluation of analogs of the marine alkaloids granulatimide and isogranulatimide

A series of pyrrolic analogs and two series of regioisomeric pyrazolic analogs of the marine alkaloids granulatimide and isogranulatimide were prepared. The synthesis of the two first ones was based on the condensation reaction of diversely 5-substituted 3-bromoindoles with pyrrole or pyrazole followed by addition of the intermediates on maleimide or dibromomaleimide, respectively, the so-obtained acyclic adducts being finally photocyclized to the desired analogs. Compounds of the last series were obtained by reacting different 5-substituted-indole-3-glyoxylates with N-Boc-pyrazole-3-acetamide and subsequent photochemical cyclization of the adducts. All the compounds were evaluated for their in vitro growth inhibitory properties toward eight cancer cell lines. Several compounds were also assayed for their ability to abrogate the G2-cell cycle checkpoint or to inhibit a panel of Ser/Thr kinases. Lastly, computer-assisted phase-contrast microscopy (quantitative videomicroscopy) revealed that the three most potent compounds (4a, 9a, 9e), with IC50 growth inhibitory concentrations ranging between 10 and 20 μM, displayed cytostatic, not cytotoxic, anticancer effects.

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Two series of regioisomeric pyrazolic analogues of the marine alkaloids granulatimide and isogranulatimide were prepared. The synthesis of the first series was based on the condensation reaction of diversely 5-substituted 3-bromoindoles with pyrazole followed by addition of the intermediates on dibromomaleimide, the so-obtained acyclic adducts being finally photochemically cyclised to the desired analogues. Compounds of the second series were obtained by reacting different 5-substituted-indole-3-glyoxylates with N-Boc-pyrazole-3-acetamide and subsequent photochemical cyclisation of the adducts.

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Starting from simple indole precursors the synthesis of naphtho[a]carbazoles and benzo[c]carbazoles is described. Key steps include the use of the Suzuki-Miyaura reaction to afford 2- or 3-aryl substituted indoles, as well as a potassium t-butoxide and light assisted aromatic ring-forming reaction.