77185-71-8

Basic information

• Product Name: 6-BROMO-2-PHENYL-1H-INDOLE
• Synonyms: 1H-INDOLE, 6-BROMO-2-PHENYL-;6-BROMO-2-PHENYL-1H-INDOLE
• CAS NO: 77185-71-8
• Molecular Formula: C₁₄H₁₀BrN
• Molecular Weight: 272.144
• Mol File: 77185-71-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 187 °C
• Boiling Point: 442.287°C at 760 mmHg
• Flash Point: 221.287°C
• Appearance: /
• Density: 1.484g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.699
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.87±0.30(Predicted)
• CAS DataBase Reference: 6-BROMO-2-PHENYL-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2-PHENYL-1H-INDOLE(77185-71-8)
• EPA Substance Registry System: 6-BROMO-2-PHENYL-1H-INDOLE(77185-71-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 77185-71-8(Hazardous Substances Data)

Usage

General Description

6-Bromo-2-phenyl-1H-indole is a chemical compound with the molecular formula C13H9BrN. It belongs to a class of organic compounds known as phenylindoles, characterized by a fused benzene and pyrrole ring forming an indole, and a phenyl group. 6-BROMO-2-PHENYL-1H-INDOLE is often used as an intermediate in the synthesis of other complex organic compounds, especially in research and development. Its specific properties depend on its purity and specific form (solid, liquid, etc.). However, it should be handled with care as it may be harmful if ingested or inhaled, and may cause skin and eye irritation. Its exact uses, safety, and environmental impacts would depend on its level of inclusion in various products or processes.

InChI:InChI=1/C14H10BrN/c15-12-7-6-11-8-13(16-14(11)9-12)10-4-2-1-3-5-10/h1-9,16H

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Relevant articles and documents

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole de

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C-H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45-85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33-94% yield).

Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

The synthesis of 6-bromo-2-arylindoles starting from readily available 2-iodobenzoic acid is presented. Regioselective bromination of the latter was followed by Curtius rearrangement and trapping of the isocyanate with benzyl alcohol led to the benzyl carbamate of 2-iodo-5-bromoaniline. Chemoselective Sonogashira coupling of this compound with arylacetylenes followed by TBAF induced 5-endo-dig cyclization gave the desired bromo indoles. The method allows selective introduction of a bromine atom at the indole C-6 position.