2,2'-Dipyridylamine

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2,2′-Dipyridylamine
Dipyridylamine.png
Names
Preferred IUPAC name
N-(Pyridin-2-yl)pyridin-2-amine
Other names
2,2′-Iminodipyridine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.013.513 Edit this at Wikidata
EC Number
  • 214-864-3
UNII
  • 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
  • C1=CC=NC(=C1)NC2=CC=CC=N2
Properties
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:
GHS07: Exclamation mark
Warning
H315, H319, H335
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).

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[edit]

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]

References[edit]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.