4,4'-Bipyridine

4,4'-Bipyridine

Names
IUPAC name 4,4'-Bipyridine
Identifiers
CAS Registry Number	553-26-4
ChEBI	CHEBI:30985
ChemSpider	10636 Y
InChI InChI=1S/C10H8N2/c1-5-11-6-2-9(1)10-3-7-12-8-4-10/h1-8H Key: MWVTWFVJZLCBMC-UHFFFAOYSA-N
Jmol-3D images	Image
SMILES C1(C2=CC=NC=C2)=CC=NC=C1
Properties
Molecular formula	C10H8N2
Molar mass	156.18 g·mol−1
Melting point	114 °C (237 °F; 387 K)
Boiling point	305 °C (581 °F; 578 K)
Structure
Dipole moment	0 D
Related compounds
Related compounds	2,2'-bipyridine Pyridine 4-Pyridylnicotinamide Terpyridine Biphenyl
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

4,4'-Bipyridine (4,4'-bipy) is a bipyridine which is mainly used as a precursor to N,N'-dimethyl-4,4'-bipyridinium [(C₅H₄NCH₃)₂]²⁺, known as paraquat. This species is electroactive, and its toxicity arises from the ability of this dication to interrupt biological electron transfer. Because of its structure, 4,4'-bipyridine can bridge between metal centres to give coordination polymers.^[1] 4,4'-bpy can also mediate electronic effects between two paramagnetic metal centers.^[2]

References