4,4'-bipyridine

Structural formula
General
Surname	4,4'-bipyridine
other names	4,4'-bipyridinyl; 4,4'-dipyridyl; 4,4'-bipyridinyl; 4,4'-dipyridine; γ, γ-bipyridine;
Molecular formula	C 10 H 8 N 2
External identifiers / databases
EC number	209-036-3
ECHA InfoCard	100.008.216
PubChem	11107
Wikidata	Q229839
properties
Molar mass	156.19 g mol −1
Physical state	firmly
Melting point	112 ° C .
boiling point	300-301 ° C
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301
	P: 260-262-309-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4,4'-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 4-position.

presentation

4,4'-bipyridine can be obtained in poor yield from the reaction of pyridine with lithium diisopropylamide and HMPT . Small amounts of 2,4'-bipyridine are formed as a by-product .

Another synthesis route consists of metal-mediated catalysis from 4-chloropyridine and pyridine or two molecules of 4-chloropyridine in the presence of a base on the nickel catalyst.

properties

At room temperature, it is a white to yellowish solid that melts at 112 ° C. and boiling at 300-301 ° C. The compound forms a dihydrate which melts incongruously at 67–70 ° C.

In the presence of metal ions , 4,4'-bipyridine can form polymeric complexes with these .

use

4,4'-bipyridine forms the basic structure of the herbicide paraquat ( N , N '-dimethyl-4,4'-bipyridinium dichloride), which can be produced from this.

Structure of paraquat

Individual evidence

↑ ^a ^b ^c Kuhnert-Brandstätter, M .; Pröll, F .: Thermal analysis of hydrates of organic compounds. I in microchim. Acta 80 (1983) 463-476.
↑ Bhat, Aparna PI; Inam, Fawad; Bhat, Badekai Ramachandra: in Eur. J. Org. Chem. 31 (2013) 7139-7144.
↑ CR Smith: Skraup's reaction applied to Phenylenediamines. Preparation of the Phenanthrolines and related Dipyridyls , in: J. Am. Chem. Soc. , 1930 , 52 , pp. 397-403; doi : 10.1021 / ja01364a061 .
↑ ^a ^b Data sheet 4,4′-bipyridine (PDF) from Merck , accessed on December 18, 2019.
↑ 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 .
↑ R. Vanderesse, M. Lourak, Y. Fort, P. Careinigung: Activation of reducing agents. Sodium hydride containing complex reducing agents 23. Symmetrical coupling of nitrogen-containing heterocyclic halides , in: Tetrahedron Letters , 1986 , 27 , pp. 5483-5486; doi : 10.1016 / S0040-4039 (00) 85243-0 .
↑ 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.

[Kuhnert-Brandstätter-1] Kuhnert-Brandstätter, M .; Pröll, F .: Thermal analysis of hydrates of organic compounds. I in microchim. Acta 80 (1983) 463-476.

[2] Bhat, Aparna PI; Inam, Fawad; Bhat, Badekai Ramachandra: in Eur. J. Org. Chem. 31 (2013) 7139-7144.

[3] CR Smith: Skraup's reaction applied to Phenylenediamines. Preparation of the Phenanthrolines and related Dipyridyls , in: J. Am. Chem. Soc. , 1930 , 52 , pp. 397-403; doi : 10.1021 / ja01364a061 .

[Merck-4] Data sheet 4,4′-bipyridine (PDF) from Merck , accessed on December 18, 2019.

[5] 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 .

[6] R. Vanderesse, M. Lourak, Y. Fort, P. Careinigung: Activation of reducing agents. Sodium hydride containing complex reducing agents 23. Symmetrical coupling of nitrogen-containing heterocyclic halides , in: Tetrahedron Letters , 1986 , 27 , pp. 5483-5486; doi : 10.1016 / S0040-4039 (00) 85243-0 .

[7] 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.