2,3'-bipyridine

Structural formula
General
Surname	2,3'-bipyridine
other names	2-pyridyl-3'-pyridine; Isonicotein; 2,3'-bipyridyl; α, β-bipyridyl;
Molecular formula	C 10 H 8 N 2
Brief description	colorless liquid
External identifiers / databases
EC number	209-468-2
ECHA InfoCard	100.008.609
PubChem	11389
Wikidata	Q209171
properties
Molar mass	156.19 g mol −1
Physical state	liquid
density	1.14 g cm −3 (20 ° C)
boiling point	295-296 ° C
Refractive index	1.6223
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	175 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2,3'-Bipyridine is a chemical compound belonging to the class of heterocycles . The alkaloid consists of two pyridine rings which are linked at positions 2 and 3 ′ to form a bipyridine .

Occurrence

2,3′-Bipyridine is one of the tobacco alkaloids and occurs naturally in tobacco plants . In a comparison of 52 smoking tobacco, 0.5–1.5 mg 2,3′-bipyridine could be detected per gram of tobacco. In addition to tobacco, the marine worms ( Hoplonemertine ) Amphiporus angulatus also contain 2,3′-bipyridine.

presentation

2,3'-bipyridine can be prepared by dehydrogenation of anabasine for example with zinc or by the dehydrogenation of anatabine by palladium are produced.

Properties and use

It is a colorless liquid that boils at 295–296 ° C. Since 2,3′-bipyridine (like the other bipyridines) is a good complexing agent, it is used for the photometric determination of Cu ²⁺ ions.

Individual evidence

↑ TT Denton, X. Zhang, JR Cashman: 5-Substituted, 6-Substituted, and Unsubstituted 3-Heteroaromatic Pyridine Analogues of Nicotine as Selective Inhibitors of Cytochrome P-450 2A6 , in: J. Med. Chem. , 2005 , 48 , Pp. 224-239.
↑ ^a ^b ^c E. Späth, S. Binietzki: N-methyl-pyrrolidine, a new tobacco alkaloid, and on the constitution of iso-nicotein , in: Chem. Ber. , 1939 , 72 , pp. 1809-1815.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Experientia. Vol. 32, Pg. 684, 1976 .
↑ Careen Merckel, Fritz Pragst : Analysis of cigarettes on additives , Institute of Forensic Medicine, Charité Berlin, 2005..
^ ^A ^b A. Townshend, DT Thorburn-Burns, E. Newman, R. Lobinski, GG Guilbault, Z. Marczenko: Dictionary of Analytical Reagents. CRC Press, 1993, ISBN 0-412-35150-1 .
↑ A. Orechoff, G. Menschikoff: About the alkaloids of Anabasis aphylla L. , in: Chem. Ber. , 1931 , 64 , pp. 266-274.
↑ E. Späth, F. Kesztler: About the occurrence of d, l-nor-nicotine, d, l-anatabine and l-anabasine in tobacco , in: Chem. Ber. , 1937 , 70 , pp. 239, 242, 704-709.

[1] TT Denton, X. Zhang, JR Cashman: 5-Substituted, 6-Substituted, and Unsubstituted 3-Heteroaromatic Pyridine Analogues of Nicotine as Selective Inhibitors of Cytochrome P-450 2A6 , in: J. Med. Chem. , 2005 , 48 , Pp. 224-239.

[spaeth-2] E. Späth, S. Binietzki: N-methyl-pyrrolidine, a new tobacco alkaloid, and on the constitution of iso-nicotein , in: Chem. Ber. , 1939 , 72 , pp. 1809-1815.

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Experientia. Vol. 32, Pg. 684, 1976 .

[5] Careen Merckel, Fritz Pragst : Analysis of cigarettes on additives , Institute of Forensic Medicine, Charité Berlin, 2005..

[dicanalyt-6] A ^b A. Townshend, DT Thorburn-Burns, E. Newman, R. Lobinski, GG Guilbault, Z. Marczenko: Dictionary of Analytical Reagents. CRC Press, 1993, ISBN 0-412-35150-1 .

[7] A. Orechoff, G. Menschikoff: About the alkaloids of Anabasis aphylla L. , in: Chem. Ber. , 1931 , 64 , pp. 266-274.

[8] E. Späth, F. Kesztler: About the occurrence of d, l-nor-nicotine, d, l-anatabine and l-anabasine in tobacco , in: Chem. Ber. , 1937 , 70 , pp. 239, 242, 704-709.