4,4'-Bipyridine
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| Template:Longitem | 113176 |
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| Template:Longitem | 2,2′-Bipyridine Pyridine 4-Pyridylnicotinamide Terpyridine Biphenyl |
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4,4′-Bipyridine (abbreviated to 4,4′-bipy or 4,4′-bpy) is an organic compound with the formula Template:Chem2. 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.
History
4,4′-Bipyridine was first obtained in 1868 by the Scottish chemist Thomas Anderson via heating pyridine with sodium metal.[1] However, Anderson's empirical formula for 4,4′-bipyridine was incorrect.[2] 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.[3]
Uses
4,4'-Bipyridine is an intermediate in the production of paraquat, a widely used herbicide. In this process, pyridine is oxidized to 4,4'-bipyridine in a coupling reaction, followed by dimethylation to form paraquat.[4]
Reactions
The reducing agent is N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene is produced by reduction of 4,4'-bipyridine in the presence of trimethylsilyl chloride (Me = CH3):
The silylated derivative, which is red, is used in salt-free reductions.[5]
4,4′-bipyridine forms a variety of coordination polymers.[6]
References
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- ↑ See:
- Script error: No such module "Citation/CS1". Anderson called 4,4′-bipyridine "Dipyridine".
- German translation: Script error: No such module "Citation/CS1".
- See also: Script error: No such module "citation/CS1". See γ-Dipyridyl.
- ↑ Anderson gave the empirical formula for 4,4′-bipyridine as C10H10N2. See:
- (Anderson, 1868), p. 209.
- (Fehling, 1890), p. 974 (γ-Dipyridyl).
- ↑ Script error: No such module "Citation/CS1". The empirical formula for 4,4′-bipyridine (γ-Dipyridyl) appears on p. 856 ; the molecular structure of 4,4′-bipyridine (γ-Dipyridyl) appears on p. 867.
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
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