2-vinyl pyridine

Structural formula
General
Surname	2-vinyl pyridine
Molecular formula	C 7 H 7 N
Brief description	light red-brown liquid with a pungent odor
External identifiers / databases
CAS number 100-69-6 EC number 202-879-8 ECHA InfoCard 100.002.618 PubChem 7521 ChemSpider 7240 Wikidata Q4596922
properties
Molar mass	105.14 g mol −1
Physical state	liquid
density	0.97 g cm −3
Melting point	−50 ° C
boiling point	159 ° C
Vapor pressure	2.5 hPa (20 ° C)
solubility	slightly soluble in water (27 g l −1 at 20 ° C) very soluble in acetone, chloroform, ethanol and methanol
Refractive index	1.549 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-302-311-314-317-411 EUH: 071 P: 210-280-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310
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 . Refractive index: Na-D line , 20 ° C

2-vinylpyridine is a chemical compound from the pyridines group .

Extraction and presentation

2-Vinylpyridine 3 can be obtained by reaction of 2-methylpyridine 1 with formaldehyde 2 and subsequent dehydration .

The compound can also be obtained from acrylonitrile by reacting with ethyne in the presence of an organocobalt catalyst:

In 1887 Albert Ladenburg synthesized 2-vinylpyridine for the first time, but did not describe a precise reaction route.

properties

2-vinylpyridine is a light red-brown liquid with a pungent odor that is sparingly soluble in water.

use

2-vinylpyridine is used in the manufacture of poly (2-vinylpyridine) by free radical polymerization as well as other polymers . It is also used to improve the effectiveness of protective polymer layers on metals and is also used as the starting material for a plastic that is used in the manufacture of pharmaceuticals and bio-compounds.

safety instructions

The vapors of 2-vinylpyridine can form an explosive mixture with air ( flash point 47 ° C, ignition temperature 440 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on 2-vinylpyridine in the GESTIS substance database of the IFA , accessed on November 22, 2018(JavaScript required) .
2. ↑ ^{a b} data sheet 2-vinylpyridines, 97%, stab. with 0.1% 4-tert-butylcatechol from AlfaAesar, accessed on November 22, 2018 ( PDF )(JavaScript required) .
3. ↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 568 ( limited preview in Google Book search).
4. ↑ Data sheet 2-vinylpyridine, 97% from Sigma-Aldrich , accessed on November 22, 2018 ( PDF ).
5. ^ Heinrich Dittmar, Manfred Drach, Ralf Vosskamp, ​​Martin E. Trenkel, Reinhold Gutser, Günter Steffens: Fertilizers, 2. Types. In: Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2009, ISBN 978-3-527-30673-2 .
6. ↑ W. Schulz, H. Pracejus, G. Oehme: New three-step synthesis of 2-vinylpyridine starting from acrylonitrile. In: Journal of Molecular Catalysis. 66, 1991, p. 29, doi : 10.1016 / 0304-5102 (91) 85018-W .
7. ↑ A. Ladenburg: About the styrene of the pyridine series. In: Reports of the German Chemical Society. 20, 1887, p. 1643, doi : 10.1002 / cber.188702001371 .
8. ↑ Google Patents: US2716118A - Process of producing vinylpyridines - Google Patents , accessed November 22, 2018.
9. ↑ Christoph Juerg Klein: On the polymerization of 2-vinylpyridine . Aku-Fotodruck, 1971, p. 12 ( limited preview in Google Book search).
10. ↑ Entry on 2-vinylpyridine in the Hazardous Substances Data Bank , accessed November 22, 2018.