2-chloropyridine
Structural formula | ||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
General | ||||||||||||||||
Surname | 2-chloropyridine | |||||||||||||||
other names |
|
|||||||||||||||
Molecular formula | C 5 H 4 ClN | |||||||||||||||
Brief description |
colorless liquid with a pyridine-like odor |
|||||||||||||||
External identifiers / databases | ||||||||||||||||
|
||||||||||||||||
properties | ||||||||||||||||
Molar mass | 113.55 g mol −1 | |||||||||||||||
Physical state |
liquid |
|||||||||||||||
density |
1.21 g cm −3 (20 ° C) |
|||||||||||||||
Melting point |
−46 ° C |
|||||||||||||||
boiling point |
170 ° C |
|||||||||||||||
Vapor pressure |
|
|||||||||||||||
solubility |
poor in water (27 g l −1 at 20 ° C) |
|||||||||||||||
Refractive index |
1.5320 (20 ° C) |
|||||||||||||||
safety instructions | ||||||||||||||||
|
||||||||||||||||
Toxicological data | ||||||||||||||||
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-chloropyridine is an organic compound that belongs to the heterocycles (more precisely: heteroaromatics ). It consists of a pyridine ring which is substituted in the 2-position with chlorine . The compound is isomeric to 3-chloropyridine and 4-chloropyridine .
presentation
In general, common electrophilic aromatic substitutions on pyridine are not possible or only possible with poor yield. Furthermore, pyridine would preferentially be substituted in the 3-position and 2-chloropyridine would only arise as a by-product. However, 2-chloropyridine can be prepared by reacting with molecular chlorine in the presence of catalytic amounts of palladium (II) chloride .
properties
2-Chloropyridine forms flammable vapor-air mixtures above the flash point of 64 ° C. The ignition temperature is 585 ° C. The substance therefore falls into temperature class T1.
use
4-Azaphenothiazine is an important intermediate for the synthesis of active substances and can be produced from 2-chloropyridine and 2-aminothiophenol .
By lithiation , 2-chloropyridine can be converted into an organolithium compound , which serves as a starting compound for other pyridine derivatives that are not directly accessible.
Individual evidence
- ↑ a b c d e f g h i j k Entry on 2-chloropyridine in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
- ↑ a b David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-112.
- ↑ Data sheet 2-chloropyridine (PDF) from Merck , accessed on March 20, 2011.
- ↑ JA Joules, K. Mills: Heterocyclic Chemistry . 4th edition, Blackwell Science, Oxford 2000, ISBN 0-632-05453-0 , pp. 77-81.
- Jump up ↑ Bernhard Kutscher, Hans Reinhold Dieter, Hans-Günther Trömer, Beate Bartz, Jürgen Engel, Axel Kleemann: New synthesis of 4-azaphenothiazine . In: Liebig's annals . tape 1995 , no. 3 , 1995, p. 591-592 , doi : 10.1002 / jlac.199519950381 .
- ↑ JA Joules, K. Mills: Heterocyclic Chemistry . 5th edition, Blackwell Publishing, Chichester 2010, ISBN 978-1-4051-9365-8 , pp. 125-141.