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4,4'-Bipyridine

Pyridine 4-Pyridylnicotinamide Terpyridine Biphenyl

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.

History

4,4′-Bipyridine was first obtained in 1868 by the Scottish chemist Thomas Anderson via heating pyridine with sodium metal.See:

  • Anderson called 4,4′-bipyridine "Dipyridine".
  • German translation:
  • See also: See γ-Dipyridyl. However, Anderson's empirical formula for 4,4′-bipyridine was incorrect.Anderson gave the empirical formula for 4,4′-bipyridine as C10H10N2. See:
  • (Anderson, 1868), p. 209.
  • (Fehling, 1890), p. 974 (γ-Dipyridyl). 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.

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.

:[[File:Paraquat synthesis.svg|578x578px]]

Reactions

The reducing agent 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.

4,4′-bipyridine forms a variety of coordination polymers.

References

References

  1. (1882). "Studien über das Pyridin". Monatshefte für Chemie.
  2. "Paraquat and Diquat". [[IPCS INCHEM]].
  3. (2019). "Salt-Free Reduction of Transition Metal Complexes by Bis(trimethylsilyl)cyclohexadiene, -dihydropyrazine, and -4,4′-bipyridinylidene Derivatives". Accounts of Chemical Research.
  4. (2006). "Crystal engineering of coordination polymers using 4,4′-bipyridine as a bond between transition metal atoms". Chemical Communications.
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bipyridines 4-pyridyl-compounds substances-discovered-in-the-19th-century symmetrical-biaryls
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