Chemistry:Tris(2-pyridylmethyl)amine
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amine_(structural_diagram).png)
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| Names | |
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| Preferred IUPAC name
1-(Pyridin-2-yl)-N,N-bis[(pyridin-2-yl)methyl]methanamine | |
| Other names
TPMA, TPA
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| Identifiers | |
3D model (JSmol)
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| ChemSpider |
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| MeSH | C431843 |
PubChem CID
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| UNII | |
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| Properties | |
| C18H18N4 | |
| Molar mass | 290.370 g·mol−1 |
| Appearance | Yellowish-pale brown solid |
| Melting point | 73 to 77 °C (163 to 171 °F; 346 to 350 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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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 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
- ↑ 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)". Inorganic Syntheses. 32. 70–75. doi:10.1002/9780470132630.ch11. ISBN 9780470132630.
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