Terpyridine (2, 2';6', 2"-terpyridine, often abbreviated to Terpy or Tpy) is a heterocyclic compound derived from pyridine. It is a white solid that is soluble in most organic solvents. The compound is mainly used as a ligand in coordination chemistry. 2-6-2 Terpyridine was first synthesized by G. Morgan and F. H. Burstall in 1932 by the oxidative coupling of pyridines. This method, however, proceeded in low yields. More efficient syntheses have since been described, mainly starting from 2-acetylpyridine. One method produces an enaminone by the reaction of 2-acetylpyridine with N, N-dimethylformamide dimethyl acetal.The base-catalyzed reaction of 2-acetylpyridine with carbon disulfide followed by alkylation with methyl iodide gives C5H4NCOCH=C(SMe)2. Condensation of this species with 2-acetylpyridine forms the related 1, 5-diketone, which condenses with ammonium acetate to form a terpyridine. Treatment of this derivative with Raney nickel removes the thioether group. Other methods have been developed for the synthesis of tpy and its substituted derivatives. Substituted terpyridines are also synthesized from palladium-catalyzed cross-coupling reactions. It can be prepared from bis-triazinyl pyridine. GFS Chemicals is a leading chemical manufacturer and supplier for 2, 2', 2"-Terpyridine in the USA.
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