189195-36-6

Basic information

• Product Name: 6'-BROMO-5-METHYL-2,2'-BIPYRIDINE
• Synonyms: 6'-BROMO-5-METHYL-2,2'-BIPYRIDINE
• CAS NO: 189195-36-6
• Molecular Formula: C₁₁H₉BrN₂
• Molecular Weight: 0
• Mol File: 189195-36-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6'-BROMO-5-METHYL-2,2'-BIPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6'-BROMO-5-METHYL-2,2'-BIPYRIDINE(189195-36-6)
• EPA Substance Registry System: 6'-BROMO-5-METHYL-2,2'-BIPYRIDINE(189195-36-6)

Safety Data

• Hazardous Substances Data: 189195-36-6(Hazardous Substances Data)

Upstream product

• 78-85-3 2-methylpropenal 
• 49669-13-8 1-(6-bromopyridin-2-yl)-ethanone 
• 77287-34-4 formamide 
• 3510-66-5 2-Bromo-5-methylpyridine 
• 626-05-1 2,6-Dibromopyridine 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 108-99-6 3-Methylpyridine 
• 189195-41-3 5-methyl-2-(tri-n-butylstannyl)pyridine 

Downstream Products

• 890936-07-9 5-(8-(4-methoxyphenyl)-1,10-phenanthrolin-3-yl)-5''-methyl-2,2':6',2''-terpyridine 

Relevant articles and documents

Synthesis of mono-, bis- and tris-tridentate ligands based on 5′-substituted-2,2′-bipyridine-6-carboxylic acid

The synthesis of 5′-methyl-2,2′-bipyridine-6-carboxylic acid is described starting from the pivotal 5′-methyl-6-bromo-2,2′-bipyridine building block. Functionalisation of the latest at the 5′-methyl position gives access to the 5′-bromomethyl, 5′-hydroxymethyl and 5′-aminomethyl derivatives. Upon nucleophilic substitution, the hydroxy and amino derivatives react with the 5′-bromomethyl compound to give quasi-linear and podand type intermediates. Thanks to a carboalkoxylation reaction at the 6-bromo position of the different intermediates, followed by a saponification reaction, mono-, bis- and tris-tridentate ligands are obtained, which are particularly well suited for the complexation of lanthanide(III) cations.

Lanthanide tags for time-resolved luminescence microscopy displaying improved stability and optical properties

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Synthesis of a novel ditopic ligand incorporating directly bonded 1,10-phenanthroline and 2,2′:6′,2″-terpyridine units

The synthesis of a rigid ditopic ligand incorporating a 1,10-phenanthroline directly connected through its 3-position to the 5-position of a 2,2′:6′,2″-terpyridine is described. The synthesis is based on a series of palladium(0)-catalyzed cross-coupling reactions (Stille and Suzuki couplings) starting from 1,10-phenanthroline and bromo-substituted pyridines.

5′-substituted-6-carboxylic-2,2′-bipyridine acid: A pivotal architecton for building preorganized ligands

A set of ligands bearing 6-bromo-2,2′-bipyridine pendant arms attached in the 5′-position are described. Transformation of the bromo to an ester was performed by a carboethoxylation reaction promoted by low-valent Pd(0), while saponification followed by acidification gave the acids. The introduction of an appended function 3-nitrobenzyl, benzamidomethyl, and tert-butylacetyl opens the way to further functionalize these scaffolds for potential labeling of biological material. The synthetic protocols represent a valuable approach to the rational design of ligands bearing oxophilic and anionic sidearms.