Tris(2-pyridylmethyl)amine

Tris(2-pyridylmethyl)amine

Names
Other names TPMA, TPA
Identifiers
CAS Number	16858-01-8 Y
3D model (JSmol)	Interactive image
ChemSpider	336061 N=
ECHA InfoCard	100.110.193
MeSH	C431843
PubChem CID	379259
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 N= Key: VGUWFGWZSVLROP-UHFFFAOYSA-N N=
SMILES c1ccnc(c1)CN(Cc2ccccn2)Cc3ccccn3
Properties
Chemical formula	C18H18N4
Molar mass	290.37 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).
N verify (what is YN ?)
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

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. 32: 70–75. doi:10.1002/9780470132630.ch11.