Tris(2-pyridylmethyl)amine explained

Tris(2-pyridylmethyl)amine (abbreviated TPMA or TPA) is an organic compound with the formula (C₅H₄NCH₂)₃N. It is a tertiary amine with three picolyl substituents. It is a white solid that is soluble in polar organic solvents. It is a ligand in coordination chemistry.

The ligand is prepared by the alkylation of 2-picolylamine by picolyl chloride:^[1]

2 C₅H₄NCH₂Cl + C₅H₄NCH₂NH₂ → (C₅H₄NCH₂)₃N + 2 HCl

TPMA is a tripodal ligand, often used to simulate the coordination environment within some proteins. It is also used as a copper ligand in ATRP.

Related ligands

• dipicolylamine, an intermediate in the synthesis of TPMA.
• 2-picolylamine, a bidentate ligand, also known as aminomethylpyridine.

References

1. Book: James W. Canary . Yihan Wang . Richard Roy, Jr. . Inorganic Syntheses . Tris[(2-Pyridyl)Methyl] Amine (TPA) and (+)-Bis[(2-Pyridyl)methyl]-1-(2-Pyridyl)-Ethylamine (α-Metpa) . . 1998 . 32 . 70–75 . 10.1002/9780470132630.ch11. 978-0-470-13263-0 .