2,4'-bipyridine

Structural formula
General
Surname	2,4'-bipyridine
other names	2-pyridyl-4'-pyridine; 2,4'-bipyridyl; 2,4'-bipyridinyl; α, γ-bipyridyl;
Molecular formula	C 10 H 8 N 2
Brief description	light yellow to light brown powder
External identifiers / databases
EC number	209-467-7
ECHA InfoCard	100.008.608
PubChem	68488
Wikidata	Q209228
properties
Molar mass	156.19 g mol −1
Physical state	firmly
Melting point	58-62 ° C
boiling point	280-282 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-335-319-312-315-332
	P: 280-302 + 352-261-301 + 312-304 + 340-280-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,4'-Bipyridine is a heterocyclic chemical compound with the empirical formula C ₁₀ H ₈ N ₂ . It consists of two pyridine rings, in which the 2-position of one ring is linked to the 4-position of the second ring and belongs to the group of bipyridines .

presentation

2,4'-Bipyridine can be prepared from 2-bromopyridine and 4-bromopyridine by a Negishi coupling . For this purpose, 2-bromopyridine is first lithiated with n- butyllithium and transmetallated to zinc organyl with the addition of zinc chloride . A palladium complex with triphenylphosphine ligands is used as the coupling catalyst .

It is also obtained in small quantities as a by-product in the synthesis of other bipyridines, for example in the production of 4,4'-bipyridine from pyridine with lithium diisopropylamide and HMPT .

properties

2,4'-Bipyridine is a yellowish solid at room temperature that melts at 58–62 ° C and boils at 280–282 ° C.

use

By reduction , 2,4'-bipyridine can be used to produce 4- (2-pyridyl) piperidine , which can be used as a starting material for further synthesis. For this purpose, the N oxide is first formed and then reduced to palladium with molecular hydrogen .

It can also be used for the synthesis of 2,2 ': 4', 2 '': 6 '', 2 '' '- quaterpyridine .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet 2,4′-bipyridine from Acros, accessed on February 21, 2013.
^ DR Sidler, N. Barta, W. Li, E. Hu, L. Matty, N. Ikemoto, JS Campbell, M. Chartrain, K. Gbewonyo, R. Boyd, EG Corley, RG Ball, RD Larsen, PJ Reider , Paul J: Efficient synthesis of the optically active dihydropyrimidinone of a potent α _1A -selective adrenoceptor antagonist. In: Canadian Journal of Chemistry . 80 (6), 2002, pp. 646-652, doi : 10.1139 / v02-079 .
↑ GR Newkome, DC Hager: Interconversion of cembranolide δ- and γ-lactones: synthesis of the C-1 epimer of isolobophytolide , in: J. Org. Chem. , 1982 , 47 , pp. 599-601 ( doi : 10.1021 / jo00342a054 ).
↑ J.-C. Plaquevant, I. Chichaoui: Réduction régiospécifique des bipyridines , in: Tetrahedron Letters , 1993 , 34 , pp. 5287-5288.
↑ JA Zoltewicz, MP Cruskie Jr., CD Dill: Use of pyridine N-oxide and pyridinium ion synthons in the preparation of oligopyridines. Two new unsymmetrical quaterpyridines with 2,2′-bipyridine units , in: Tetrahedron , 1996 , 52 , pp. 4239-4244 ( doi : 10.1016 / 0040-4020 (96) 00100-7 ).

[acros-1] ↑ ^a ^b ^c ^d ^e data sheet 2,4′-bipyridine from Acros, accessed on February 21, 2013.

[2] DR Sidler, N. Barta, W. Li, E. Hu, L. Matty, N. Ikemoto, JS Campbell, M. Chartrain, K. Gbewonyo, R. Boyd, EG Corley, RG Ball, RD Larsen, PJ Reider , Paul J: Efficient synthesis of the optically active dihydropyrimidinone of a potent α _1A -selective adrenoceptor antagonist. In: Canadian Journal of Chemistry . 80 (6), 2002, pp. 646-652, doi : 10.1139 / v02-079 .

[3] GR Newkome, DC Hager: Interconversion of cembranolide δ- and γ-lactones: synthesis of the C-1 epimer of isolobophytolide , in: J. Org. Chem. , 1982 , 47 , pp. 599-601 ( doi : 10.1021 / jo00342a054 ).

[4] J.-C. Plaquevant, I. Chichaoui: Réduction régiospécifique des bipyridines , in: Tetrahedron Letters , 1993 , 34 , pp. 5287-5288.

[5] JA Zoltewicz, MP Cruskie Jr., CD Dill: Use of pyridine N-oxide and pyridinium ion synthons in the preparation of oligopyridines. Two new unsymmetrical quaterpyridines with 2,2′-bipyridine units , in: Tetrahedron , 1996 , 52 , pp. 4239-4244 ( doi : 10.1016 / 0040-4020 (96) 00100-7 ).