66127-00-2

Usage

Uses

Used in Chemical Synthesis:
3,5,6,8-TETRABROMO-[1,10]PHENANTHROLINE is used as a reagent in the nickel-catalyzed amination of aryl and heteroaryl chlorides. This application is particularly relevant in the field of organic chemistry, where the compound plays a crucial role in facilitating the formation of new chemical bonds and the synthesis of complex organic molecules.
In the nickel-catalyzed amination process, 3,5,6,8-TETRABROMO-[1,10]PHENANTHROLINE acts as a ligand, coordinating with the nickel catalyst and enhancing its catalytic activity. This results in the efficient coupling of aryl and heteroaryl chlorides with amines, leading to the formation of aminated products. These products are valuable intermediates in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
The use of 3,5,6,8-TETRABROMO-[1,10]PHENANTHROLINE in this application offers several advantages, including improved reaction efficiency, selectivity, and mild reaction conditions. It also allows for the synthesis of a wide range of aminated products with diverse functional groups and structural features, expanding the scope of chemical synthesis and enabling the development of new and innovative molecules with potential applications in various industries.
Overall, 3,5,6,8-TETRABROMO-[1,10]PHENANTHROLINE is a versatile and valuable compound with significant applications in the field of chemical synthesis, particularly in the nickel-catalyzed amination of aryl and heteroaryl chlorides. Its unique properties and reactivity make it an essential component in the development of new synthetic methods and the production of a broad range of chemical products.

Upstream product

• 860193-85-7 3,5,6-tribromo-[8]quinolylamine 
• 408529-03-3 3,3-diacetoxy-2-bromo-propene 
• 66-71-7 1,10-Phenanthroline 
• 651733-22-1 3,5,6-tribromo-8-nitro-quinoline 
• 24108-97-2 3,4-dibromoacetanilide 
• 75293-96-8 acetic acid-(4,5-dibromo-2-nitro-anilide) 

Downstream Products

• 804565-42-2 ZnCl₂(N₂C₁₂H₄(C₂C₆H₅)4) 
• 1086033-76-2 3,5,6,8-tetra(4-tert-butylphenyl)-1,10-phenanthroline 
• 1086033-74-0 3,5,6,8-tetra(para-biphenyl)-1,10-phenanthroline 
• 1086033-72-8 3,5,6,8-tetraphenyl-1,10-phenanthroline 

Relevant academic research and scientific papers

Regioselective functionalization of tetrabromophenanthroline-ruthenium complexes

Structural, photophysical and photochemical characterization and reactivity of a novel polypyridyl ruthenium complex based on 3,5,6,8- tetrabromophenanthroline are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Novel and simple synthesis of brominated 1,10-phenanthrolines

A novel, simple, and reasonably efficient synthesis of 3,8-dibromo-1,10- phenanthroline, 3,6-dibromo-1,10-phenanthroline, 3,5,8-tribromo-1,10- phenanthroline, and 3,5,6,8-tetrabromo-1,10-phenanthroline is presented herein. The crucial role of a new catalyst (sulfur dichloride-SCl2) for the bromination of 1,10-phenanthroline is reported. The bromination of 1,10-phenanthroline monohydrate in the presence of SCl2 and pyridine yielded the brominated compounds, previously only possible through the complicated multi-step and tedious Skraup synthesis method. The application of the bromination catalyst SCl2 as a medium-strength Lewis acid is demonstrated for the first time, and the results are compared with the behaviours of known weak (sulfur chloride-S2Cl2) and strong (thionyl chloride-SOCl2) bromination catalysts. A reaction mechanism was proposed. CSIRO 2014.

An efficient silane-promoted nickel-catalyzed amination of aryl and heteroaryl chlorides

(Chemical Equation Presented) A new silane-promoted nickel-catalyzed amination of aryl chlorides with 0.5 mol % of Ni(acac)2, 1 mol % of 3,5,6,8-tetrabromo-1,10-phenanthroline, and polymethylhydrosiloxane was developed. A broad range of aryl and heteroaryl chlorides can be coupled with secondary amines and anilines to give the desired (het)arylamines in good to excellent yields. The reaction is sensitive to the nature and amount of the silane promoter.