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Tris(2-pyridylmethyl)amine

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Tris(2-pyridylmethyl)amine
Names
Preferred IUPAC name 1-(Pyridin-2-yl)-N,N-bismethanamine
Other names TPMA, TPA
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.110.193 Edit this at Wikidata
MeSH C431843
PubChem CID
UNII
CompTox Dashboard (EPA)
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
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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:

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

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)". Inorganic Syntheses. Vol. 32. pp. 70–75. doi:10.1002/9780470132630.ch11. ISBN 978-0-470-13263-0. {{cite book}}: |journal= ignored (help)
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