3,4'-bipyridine

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Structural formula
Structural formula of 3,4′-bipyridine
General
Surname 3,4'-bipyridine
other names
  • 3,4'-bipyridinyl
  • 3,4'-dipyridyl
  • 3,4'-bipyridinyl
  • 3,4'-dipyridine
  • β, γ-bipyridine
Molecular formula C 10 H 8 N 2
External identifiers / databases
CAS number 4394-11-0
PubChem 11355618
Wikidata Q222998
properties
Molar mass 156.19 g mol −1
Physical state

firmly

Melting point

63-65 ° C

boiling point

115 ° C (at 4 h Pa )

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,4′-Bipyridine is a heterocyclic chemical compound with the empirical formula C 10 H 8 N 2 . It consists of two pyridine rings, the 3-position of one being linked to the 4-position of the second ring.

presentation

3,4'-Bipyridine can be prepared in good yield from 3-bromopyridine and a 4-pyridyl stannane in a palladium- catalyzed Stille coupling .

Synthesis of 3,4′-bipyridine via Stille coupling

Another synthetic route is a Suzuki coupling between 4-chloropyridine and a 3-pyridyl-substituted boronic acid ester .

Individual evidence

  1. ↑ M. Ishikura, T. Ohta, M. Terashima: A Novel Synthesis of 4-Aryl-and 4-Heteroarylpyridines via Diethyl (4-pyridyl) borane. In: Chemical & Pharmaceutical Bulletin . 33, 1985, pp. 4755-4763.
  2. ↑ a b Y. Yamamoto, Y. Azuma, H. Mitoh: General Method for Synthesis of Bipyridines: Palladium Catalyzed Cross-coupling Reaction of Trimethylstannyl-pyridines with Bromopyridines. In: Synthesis . 1986, pp. 564-565. doi: 10.1055 / s-1986-31705 .
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ N. Kudo, M. Perseghini, GC Fu: A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles. In: Angew. Chem. 118, 2006, pp. 1304-1304. doi: 10.1002 / anie.200503479 .