Tris(2-pyridylmethyl)amine

Tris(2-pyridylmethyl)amine
Names
	Other names TPMA, TPA
Identifiers
CAS Number	16858-01-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	336061 =;
ECHA InfoCard	100.110.193
MeSH	C431843
PubChem CID	379259;
CompTox Dashboard (EPA)	DTXSID70327519 ;
	InChI InChI=1S/C18H18N4/c1-4-10-19-16(7-1)13-22(14-17-8-2-5-11-20-17)15-18-9-3-6-12-21-18/h1-12H,13-15H2 = Key: VGUWFGWZSVLROP-UHFFFAOYSA-N =;
	SMILES c1ccnc(c1)CN(Cc2ccccn2)Cc3ccccn3;
Properties
Chemical formula	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).
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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). Inorg. Synth. Inorganic Syntheses. 32. pp. 70–75. doi:10.1002/9780470132630.ch11. ISBN 9780470132630.

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[1] 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. Inorganic Syntheses. 32. pp. 70–75. doi:10.1002/9780470132630.ch11. ISBN 9780470132630.