4,4′-bipyridine

Also known as gamma,gamma'-bipyridyl, gamma,gamma'-dipyridyl, 4,4'-dipyridyl, 4,4'-dipyridine, 4,4'-bipyridyl, 4,4'-bpy, 4,4-Bipyridin, 4-(4-pyridyl)pyridine

4,4′-Bipyridine (abbreviated to 4,4′-bipy or 4,4′-bpy) is an organic compound with the formula . It is one of several isomers of bipyridine. It is a colorless solid that is soluble in organic solvents. is mainly used as a precursor to N,N′-dimethyl-4,4′-bipyridinium [(C5H4NCH3)2]2+, known as paraquat.

Chemical data

Formula: C10H8N2
Molecular weight: 156.18 g/mol
IUPAC name: 4-pyridin-4-ylpyridine
SMILES: C1=CN=CC=C1C2=CC=NC=C2
InChIKey: MWVTWFVJZLCBMC-UHFFFAOYSA-N
XLogP: 1.4
Polar surface area: 25.8 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of: bipyridine
Has part: hydrogen
Mass: 156.069

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chemical formula: C₁₀H₈N₂
canonical SMILES: C1=CN=CC=C1C2=CC=NC=C2
MCN code: 2933.39.94
melting point: 113.0
has characteristic: bitterness
Commons category: 4,4'-Bipyridine

Sources (4)

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Encyclopedic overview

4 sections

Contents

History
Uses
Reactions
References

==History== 4,4′-Bipyridine was first obtained in 1868 by the Scottish chemist Thomas Anderson via heating pyridine with sodium metal. However, Anderson's empirical formula for 4,4′-bipyridine was incorrect. The correct empirical formula, and the correct molecular structure, for 4,4′-bipyridine was provided in 1882 by the Austrian chemist Hugo Weidel and his student M. Russo.

Excerpted from Wikipedia’s “4,4′-bipyridine” article, available under the CC BY-SA 4.0 licence.