2,2'-bipyridine

Structural formula
General
Surname	2,2'-bipyridine
other names	2,2'-bipyridinyl; α-bipyridyl; α, α'-dipyridyl; bipy;
Molecular formula	C 10 H 8 N 2
Brief description	colorless crystals with a faint odor
External identifiers / databases
EC number	206-674-4
ECHA InfoCard	100.006.069
PubChem	1474
Wikidata	Q209143
properties
Molar mass	156.19 g mol −1
Physical state	firmly
Melting point	70-72 ° C
boiling point	272 ° C
solubility	poor in water (5.5 g l −1 at 22 ° C)
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301 + 311
	P: 280-301 + 310 + 330-302 + 352 + 312
Toxicological data	100 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

presentation

2,2'-pyridine can be synthesized from pyridine at 330 ° C with iron (III) chloride or at room temperature with Raney nickel . Another simple synthesis route is the Ullmann coupling of 2-bromopyridine , for which copper dust is used.

properties

2,2'-Bipyridine is a white solid at room temperature that melts at 70-72 ° C and boils at 272 ° C. The compound can be used as a bidentate chelating ligand and coordinates via the nitrogen atoms. The abbreviation bipy is often used as a ligand . Stable complexes are formed with many transition metals . With octahedral complex geometry, two enantiomeric complex species are formed .

use

The complex of 2,2′-bipyridine with divalent iron ([Fe (bipy) ₃ ] ²⁺ ) is deep red in solution . This complex can be used for the quantitative colorimetric determination of iron. Ferric iron can predict, for example, sodium hydrogen sulfite , or ascorbic acid , reducing be.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on 2,2′-bipyridyl in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ Data Sheet 2,2'-bipyridine (PDF) at Merck , accessed on 21 November 2008 .
↑ F. Hein, H. Schwedler: On the α, α-dipyridyl synthesis from pyridine and iron (III) chloride, and on some dipyridyl complex salts , in: Chem. Ber. , 68, 1935, pp. 681-684; doi : 10.1002 / cber.19350680425 .
^ WHF Sasse: 2,2′-bipyridine In: Organic Syntheses . 46, 1966, pp. 5-8, doi : 10.15227 / orgsyn.046.0005 ; Coll. Vol. 5, 1973, p. 102 ( PDF ).
^ FH Burstall: Researches on the polypyridyls , in: J. Chem. Soc. , 1938, pp. 1662-1671; doi : 10.1039 / JR9380001662 .
↑ G.-O. Müller: Quantitative-inorganic internship . 7th edition, p. 376, Verlag Harri Deutsch, Frankfurt / Main 1992, ISBN 3-8171-1211-4 .

[gestis-1] ↑ ^a ^b ^c ^d ^e ^f Entry on 2,2′-bipyridyl in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[merck-2] Data Sheet 2,2'-bipyridine (PDF) at Merck , accessed on 21 November 2008 .

[3] F. Hein, H. Schwedler: On the α, α-dipyridyl synthesis from pyridine and iron (III) chloride, and on some dipyridyl complex salts , in: Chem. Ber. , 68, 1935, pp. 681-684; doi : 10.1002 / cber.19350680425 .

[4] WHF Sasse: 2,2′-bipyridine In: Organic Syntheses . 46, 1966, pp. 5-8, doi : 10.15227 / orgsyn.046.0005 ; Coll. Vol. 5, 1973, p. 102 ( PDF ).

[5] FH Burstall: Researches on the polypyridyls , in: J. Chem. Soc. , 1938, pp. 1662-1671; doi : 10.1039 / JR9380001662 .

[6] G.-O. Müller: Quantitative-inorganic internship . 7th edition, p. 376, Verlag Harri Deutsch, Frankfurt / Main 1992, ISBN 3-8171-1211-4 .