2,2'-Dipyridylamine

2,2′-Dipyridylamine
Names
	Preferred IUPAC name N-(Pyridin-2-yl)pyridin-2-amine
	Other names 2,2′-Iminodipyridine
Identifiers
CAS Number	1202-34-2;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1735909;
ChemSpider	13888;
ECHA InfoCard	100.013.513
EC Number	214-864-3;
PubChem CID	14547;
UNII	X9BF664YAK;
CompTox Dashboard (EPA)	DTXSID5061619;
	InChI InChI=1S/C10H9N3/c1-3-7-11-9(5-1)13-10-6-2-4-8-12-10/h1-8H,(H,11,12,13) Key: HMMPCBAWTWYFLR-UHFFFAOYSA-N;
	SMILES C1=CC=NC(=C1)NC2=CC=CC=N2;
Properties
Chemical formula	C10H9N3
Molar mass	171.203 g·mol−1
Appearance	white solid
Melting point	90.5 °C (194.9 °F; 363.6 K)
Boiling point	307.5 °C (585.5 °F; 580.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1] Its conjugate base, 2,2′-dipyridylamide, forms extended metal atom chains.^[2]

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.^[3]

^ Wang, Suning (2001). "Luminescence and electroluminescence of Al(III), B(III), Be(II) and Zn(II) complexes with nitrogen donors". Coordination Chemistry Reviews. 215: 79–98. doi:10.1016/S0010-8545(00)00403-3.
^ Cotton, F. Albert; Daniels, Lee M.; Jordan; Murillo, Carlos A. (1997). "Symmetrical and Unsymmetrical Compounds Having a Linear Co₃⁶⁺ Chain Ligated by a Spiral Set of Dipyridyl Anions". Journal of the American Chemical Society. 119 (43): 10377–10381. doi:10.1021/JA971997H.
^ Brogden, David W.; Berry, John F. (4 September 2015). "Coordination Chemistry of 2,2′-Dipyridylamine: The Gift That Keeps on Giving". Comments on Inorganic Chemistry. 36 (1): 17–37. doi:10.1080/02603594.2015.1079522. S2CID 101638568.