3,3'-bipyridine

Structural formula
General
Surname	3,3'-bipyridine
other names	3,3'-bipyridinyl; 3,3'-dipyridyl; 3,3'-bipyridinyl;
Molecular formula	C 10 H 8 N 2
External identifiers / databases
EC number	209-466-1
ECHA InfoCard	100.008.607
PubChem	68487
Wikidata	Q222984
properties
Molar mass	156.19 g mol −1
Physical state	firmly
Melting point	68 ° C
boiling point	300-301 ° C
safety instructions
GHS hazard labeling ; no classification available
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 .

3,3′-Bipyridine is a heterocyclic chemical compound with the empirical formula C ₁₀ H ₈ N ₂ . It consists of two pyridine rings that are linked to one another in the 3-position.

presentation

A synthesis of 3,3′-bipyridine involves the metal-mediated catalytic coupling of two molecules of 3-chloropyridine using a base . A nickel complex serves as the catalyst .

It can also be synthesized from the corresponding 3-pyridyl starting materials by a Stille or Suzuki coupling .

properties

At room temperature, it is a white to yellowish solid that melts at 109–112 ° C and boils at 305 ° C.

In contrast to 2,2′-bipyridine , 3,3′-bipyridine is not a chelating ligand , as the two nitrogen atoms are positioned in such a way that, for geometric reasons, they cannot both coordinate at the same metal center .

Individual evidence

↑ ^a ^b entry on 3,3′-bipyridine . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed July 13, 2012.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Y. Fort, S. Becker, P. Ca Clean: A convenient synthetic route to bis-heteroaromatic and bis-heterocyclic compounds promoted by liganded nickel complex reducing agents. , in: Tetrahedron , 1994 , 50 , pp. 11893-11902.
^ E. Rajalakshmanan, V. Alexander: Synthesis of Dimethylbipyridines by the Reductive Coupling of 2-Halomethylpyridines with Nickel Catalyst , in: Synth. Comm. , 2005 , 35 , pp. 891-895; doi : 10.1081 / SCC-200051056 .
↑ Y. Yamamoto, Y. Azuma, H. Mitoh, Hiroyuki: General Method for Synthesis of Bipyridines: Palladium Catalyzed Cross-coupling Reaction of Trimethylstannyl-pyridines with Bromopyridines , in: Synthesis , 1986 , 13 , pp. 564-565; doi : 10.1055 / s-1986-31705 .
↑ M. Ishikura, M. Kamada, M. Terashima: An Efficient Synthesis of 3-Heteroarylpyridines via Diethyl- (3-pyridyl) -borane , in: Synthesis , 1984 , 11 , pp. 936-938; doi : 10.1055 / s-1984-31026 .

[NIST-1] try on 3,3′-bipyridine . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed July 13, 2012.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Y. Fort, S. Becker, P. Ca Clean: A convenient synthetic route to bis-heteroaromatic and bis-heterocyclic compounds promoted by liganded nickel complex reducing agents. , in: Tetrahedron , 1994 , 50 , pp. 11893-11902.

[4] E. Rajalakshmanan, V. Alexander: Synthesis of Dimethylbipyridines by the Reductive Coupling of 2-Halomethylpyridines with Nickel Catalyst , in: Synth. Comm. , 2005 , 35 , pp. 891-895; doi : 10.1081 / SCC-200051056 .

[5] Y. Yamamoto, Y. Azuma, H. Mitoh, Hiroyuki: General Method for Synthesis of Bipyridines: Palladium Catalyzed Cross-coupling Reaction of Trimethylstannyl-pyridines with Bromopyridines , in: Synthesis , 1986 , 13 , pp. 564-565; doi : 10.1055 / s-1986-31705 .

[6] M. Ishikura, M. Kamada, M. Terashima: An Efficient Synthesis of 3-Heteroarylpyridines via Diethyl- (3-pyridyl) -borane , in: Synthesis , 1984 , 11 , pp. 936-938; doi : 10.1055 / s-1984-31026 .