2,2′-Bipyridine

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2,2′-Bipyridine
Skeletal formula of 2,2′-bipyridine
Ball-and-stick model of the 2,2′-bipyridine molecule
Space-filling model of the 2,2′-bipyridine molecule
Names
Preferred IUPAC name
2,2′-Bipyridine
Other names
Bipyridyl
Dipyridyl
Bipy
Bpy
Dipy
Identifiers
3D model (
JSmol
)
113089
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.006.069 Edit this at Wikidata
EC Number
  • 206-674-4 923-456-0
3720 936807
RTECS number
  • DW1750000
UNII
  • InChI=1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H checkY
    Key: ROFVEXUMMXZLPA-UHFFFAOYSA-N checkY
  • InChI=1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H
    Key: ROFVEXUMMXZLPA-UHFFFAOYAP
  • n1ccccc1-c2ccccn2
Properties
C10H8N2
Molar mass 156.188 g·mol−1
Appearance Colorless solid
Melting point 70 to 73 °C (158 to 163 °F; 343 to 346 K)
Boiling point 273 °C (523 °F; 546 K)
Structure
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H302, H311, H312, H319, H412
P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P337+P313, P361, P363, P405, P501
Lethal dose or concentration (LD, LC):
15-78 mg/kg (oral, rat); 20-140 mg/kg (oral, mouse)
Related compounds
Related compounds
Phenanthroline
3-Pyridylnicotinamide
Terpyridine
Biphenyl
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

2,2′-Bipyridine (bipy or bpy, pronounced

bidentate chelating ligand, forming complexes with many transition metals. Ruthenium and platinum complexes of bipy exhibit intense luminescence
, which may have practical applications.

Preparation, structure, and general properties

2,2'-Bipyridine was first prepared by decarboxylation of divalent metal derivatives of

pyridine-2-carboxylate:[1]

M(O2CC5H4N)2 → (C5H4N)2 + 2 CO2 + ...

It is prepared by the dehydrogenation of pyridine using Raney nickel:[2]

2 C5H5N → (C5H4N)2 + H2

Substituted 2,2'-bipyridines

Unsymmetrically substituted 2,2'-bipyridines can be prepared by

cross coupling reaction of 2-pyridyl and substituted pyridyl reagents.[3]

Structure

Although bipyridine is often drawn with its nitrogen atoms in cis conformation, the lowest energy conformation both in solid state and in solution is in fact coplanar, with nitrogen atoms in trans position.[4] Monoprotonated bipyridine adopts a cis conformation.[5]

Reactions

A large number of complexes of 2,2'-bipyridine have been described. It binds metals as a chelating ligand, forming a 5-membered chelate ring.

See also

References

  1. PMID 31683694
    .
  2. ^ Sasse, W. H. F. (1966). "2,2′-Bipyridine". Organic Syntheses. 46: 5; Collected Volumes, vol. 5, p. 102.
  3. doi:10.15227/orgsyn.089.0076
    .
  4. doi:10.1107/S0365110X56002175
    .
  5. doi:10.1016/S0009-2614(00)00352-3
    .
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