Description
2,2′-Dipyridylamine is an organic compound with the formula (C5H4N)2NH. It consists of a pair of 2-pyridyl groups (C5H4N) linked to a secondary amine. The compound forms a range of coordination complexes.Its conjugate base, 2,2′-dipyridylamide, forms extended metal atom chains.
Synthesis
Tri-tert-butylphosphine, palladium acetate, and sodium tert-butoxide were added to a solution of 2-aminopyridine and 2-bromopyridine in degassed toluene, and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled to room temperature, diluted with toluene, and filtered through diatomaceous earth. The filtrate was diluted with water, extracted with toluene, and the organic phases were combined and evaporated under vacuum. The residue was filtered through silica gel and then repurified to give 2,2'-DIPYRIDYLAMINE.
Formation
2,2′-Dipyridylamine can be formed by heating pyridine with sodium amide. Alternatively, 2-aminopyridine can be heated with 2-chloropyridine over barium oxide.
Chemical Properties
White solid
Uses
2,2′-Dipyridylamine (bipyam) can be used:
- As a bidentate N-donor ligand in the synthesis of various metal complexes.
- To synthesize Pd-polyoxovanadates, heterogeneous catalyst for the oxidation of benzylic hydrocarbons.
Uses
A metal-complexing agent; an effective iron chelating agent to help protect against UVB radiation. An impurity of Chlorpheniramine Maleate (C424300).
General Description
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Purification Methods
Crystallise the amine from *benzene or toluene [Blakley & De Armond J Am Chem Soc 109 4895 1987]. The amine is also recrystallised from Me2CO (m 95.1o) or distilled in a vacuum. [Beilstein 22 I 630, 22 II 331, 22 III/IV 3961.]
