393553-57-6

Basic information

• Product Name: 6-BROMO-4-METHOXYINDOLE
• Synonyms: 6-BROMO-4-METHOXYINDOLE;1H-Indole, 6-broMo-4-Methoxy-;6-broMo-4-Methoxy-1H-indole;6-BroMo-4-Methoxy-1h-indol
• CAS NO: 393553-57-6
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.07
• Mol File: 393553-57-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 346.8°Cat760mmHg
• Flash Point: 163.5°C
• Appearance: /
• Density: 1.591g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.29±0.30(Predicted)
• CAS DataBase Reference: 6-BROMO-4-METHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-4-METHOXYINDOLE(393553-57-6)
• EPA Substance Registry System: 6-BROMO-4-METHOXYINDOLE(393553-57-6)

Safety Data

• Hazardous Substances Data: 393553-57-6(Hazardous Substances Data)

Usage

General Description

6-Bromo-4-methoxyindole is a chemical compound with the molecular formula C9H8BrNO. It is an indole derivative with a bromine atom at the 6th position and a methoxy group at the 4th position. 6-BROMO-4-METHOXYINDOLE is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. It is also used in research and development as a reagent in organic and medicinal chemistry. 6-Bromo-4-methoxyindole has potential applications in the development of new drugs and can also be used as a starting material for the synthesis of complex organic molecules.

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

Upstream product

• 606-20-2 2,6-dinitrotoluene 
• 95192-64-6 5-bromo-2-methyl-1,3-dinitrobenzene 
• 864550-40-3 5-bromo-2-methyl-3-nitroaniline 
• 864550-41-4 5-bromo-2-methyl-3-nitrophenol 
• 885519-07-3 5-bromo-1-methoxy-2-methyl-3-nitrobenzene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 43192-33-2 4-bromo-2-methoxybenzaldehyde 
• 67-56-1 methanol 
• 52415-29-9 6-bromo-1H-indole 

Downstream Products

• 1181566-81-3 6-ethenyl-4-(methyloxy)-1H-indole 
• 1202766-19-5 6-bromo-4-methoxy-1H-indole-3-carbaldehyde 
• 61-54-1 tryptamine 
• 1181566-83-5 6-ethenyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole 
• 1181566-85-7 6-ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole 
• 1181566-57-3 6-ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol 

Relevant articles and documents

C4?H alkoxylation of 6-bromoindole and its application to the synthesis of breitfussin B

Subjecting 6-bromoindole to an iridium-catalysed triborylation-diprotodeborylation sequence followed by Chan-Evans-Lam coupling gives 6-bromo-4-methoxyindole in good overall yield. This indole C4?H alkoxylation process was used in a formal synthesis of the natural product breitfussin B.

A Concise Total Synthesis of Breitfussin A and B

(Chemical Equation Presented). The first total synthesis of breitfussin A and B is described. The approach features two palladium-catalyzed cross-couplings installing the indole and pyrrole onto the oxazole core and selective lithiation/iodination of a common indole-oxazole fragment providing 2,4-diiodinated or 2-iodinated oxazoles as potential precursors for breitfussin A and B, respectively. An unexpected acid promoted deiodination was utilized in the synthesis of breitfussin B. Comparison of the synthetic material with previously reported spectral data of isolated breitfussin A and B verified the structure of the breitfussin framework.