Terpyridine

• 2,6-bis (2-pyridyl ) pyridine
• 2,2 ': 6', 2''- terpyridine
• Terpy

• White, odorless prisms
• Yellow needles (as picrate )

Fixed

• 89-92 ° C
• 210 ° C ( picrate )

370 ° C.

• Poorly in cold, better in warm water
• Soluble in many organic solvents
• Insoluble in petroleum ether

Risk

1.99 mg · kg -1 ( LD50, rat, oral)

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Terpyridine is a heterocyclic chemical compound with the molecular formula C15H11N3. It consists of three pyridine rings, each of which is in the 2- positions or 2,6- positions are linked.

Synthesis

Terpyridine was first obtained in 1932 by the oxidative coupling of pyridine in the presence of iron ( III) chloride at 340 ° C in an autoclave. The result is a product mixture of various pyridine derivatives, bipyridines and Quaterpyridin, which also contains terpyridine. By reacting 2 -bromopyridine with 2,6- dibromopyridine with copper in the sense of an Ullmann coupling terpyridine can be produced with higher selectivity.

There is a number of recent synthetic routes known which often on palladium - catalyzed coupling reactions are based ( Hiyama coupling, Stille coupling, Negishi coupling )

Properties

Terpyridine is a chelating ligand, which with many transition metals complexes of the form [M ( terpy ) 2] n forms.

In the context of the safe disposal of radioactive waste process for the separation (partitioning ) of nuclear material are currently being investigated in groups of elements. Here, the separation of actinides and lanthanides chemically similar the Minor is required. Terpyridine this was the first ligand which could this separation, although with a moderate separation factor of 7 to accomplish. Meanwhile exist for this purpose, however, significantly more selective extractants.