2,2'-bipyridine
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | 2,2'-bipyridine | |||||||||||||||
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Molecular formula | C 10 H 8 N 2 | |||||||||||||||
Brief description |
colorless crystals with a faint odor |
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properties | ||||||||||||||||
Molar mass | 156.19 g mol −1 | |||||||||||||||
Physical state |
firmly |
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Melting point |
70-72 ° C |
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boiling point |
272 ° C |
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solubility |
poor in water (5.5 g l −1 at 22 ° C) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
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 .