1,4,7-Triazacyclononane

1,4,7-Triazacyclononane (also known as TACN or triazanonane) is a heterocyclic compound consisting of a nine-membered ring containing three nitrogen atoms at positions 1, 4, and 7. This compound is a macrocyclic ligand and is used in the formation of various coordination compounds.

Structure and Properties

al;t=1,4,7-triazacyclononane

• 1,4,7-Triazacyclononane is a symmetric, non-aromatic, nine-membered ring. The three nitrogen atoms are equally spaced around the ring, resulting in a trigonal planar geometry. This compound is a cyclic amine, with the nitrogen atoms acting as donor atoms in coordination chemistry.

• The molecular formula of 1,4,7-Triazacyclononane is C6H12N3, and its molar mass is 126.18 g/mol. It is a colorless, crystalline solid at room temperature.

Synthesis

1,4,7-Triazacyclononane can be synthesized from diaminopropane via a Mannich reaction. The resulting product is a tertiary amine, which can then be cyclized to form the nine-membered ring.

Applications

1,4,7-Triazacyclononane is primarily used in the synthesis of coordination compounds. It acts as a tridentate ligand, binding to metal ions via the three nitrogen atoms. This makes it useful in the creation of catalysts and in nuclear medicine for the production of radiopharmaceuticals.

See Also

• Macrocyclic ligand
• Coordination compound
• Mannich reaction
• Nuclear medicine