Tris(2-pyridylmethyl)amine
amine_(structural_diagram).png) | |
| Names | |
|---|---|
| Other names
TPMA, TPA | |
| Identifiers | |
16858-01-8  | |
| Properties | |
| Molecular formula |
C18H18N4 |
| Molar mass | 290.36 g·mol−1 |
| Appearance | Yellowish-pale brown solid |
| Melting point | 73 to 77 °C (163 to 171 °F; 346 to 350 K) |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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| Infobox references | |
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 picolylamine by picolyl chloride:[1]
- 2 C5H4NCH2Cl + C5H4NCH2NH2 → (C5H4NCH2)3N + 2 HCl
TPA is a tripodal ligand, often used to simulate the coordination environment within some proteins. It is also used as a copper ligand in ATRP. A related ligand is dipicolylamine, which in fact is an intermediate in the synthesis of TPA.
References
- ↑ James W. Canary, Yihan Wang, Richard Roy, Jr. (1998). "Tris[(2-Pyridyl)Methyl] Amine (TPA) and (+)-Bis[(2-Pyridyl)methyl]-1-(2-Pyridyl)-Ethylamine (α-Metpa)". Inorg. Synth. 32: 70–75. doi:10.1002/9780470132630.ch11.