4-chloropyridine

Structural formula
General
Surname	4-chloropyridine
other names	p -chloropyridine
Molecular formula	C 5 H 4 ClN
Brief description	colorless liquid with a pyridine-like odor
External identifiers / databases
EC number	210-956-2
ECHA InfoCard	100.009.961
PubChem	12288
Wikidata	Q229945
properties
Molar mass	113.55 g mol −1
Physical state	liquid
Melting point	−43.5
boiling point	147 ° C
Dipole moment	0.84 D
Refractive index	1.5315
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	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

4-chloropyridine is an organic compound that belongs to the heterocycles (more precisely: heteroaromatics ). It consists of a pyridine ring which is substituted in the 4-position with chlorine . The compound is isomeric to 2-chloropyridine and 3-chloropyridine .

presentation

For the preparation of 4-chloropyridine may pyridine N oxide with thionyl chloride are reacted.

The reaction of 4-thiopyridone , which can be obtained by reacting 4-pyridone with phosphorus pentasulfide , with chlorine also leads to 4-chloropyridine.

The direct chlorination of pyridine- N -oxide with phosphoryl chloride gives 2-chloropyridine as the main product and 4-chloropyridine as a by-product.

use

4-chloropyridine, in a metal-mediated catalysis of pyridine Synthesis of 4,4'-bipyridine are used. This in turn represents a basic chemical substance, for example for the production of the herbicide paraquat .

For the synthesis of the isomeric 3,4'-bipyridine , 4-chloropyridine can be reacted with a 3-pyridyl-substituted boronic acid ester in a Suzuki coupling .

Individual evidence

↑ ^a ^b H. King, LL Ware: 4 – Thiopyridone and derived substances , in: J. Chem. Soc. , 1939 , pp. 873-877; doi : 10.1039 / JR9390000873 .
↑ 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.
↑ CWN Cumper, AI Vogel: Physical properties and chemical constitution. Part XXX. The dipole moments of some halogeno- and cyano-pyridines , in: J. Chem. Soc. , 1960 , pp. 4723-4728; doi : 10.1039 / JR9600004723 .
^ ^A ^b D. G. Leis, B. Columba Curran: Electric Moments of Some γ-Substituted Pyridines , in: J. Am. Chem. Soc. , 1945 , 67 , pp. 79-81; doi : 10.1021 / ja01217a028 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ B. Bobranacuteski, L. Kochanacuteska, A. Kowalewska: On the action of sulfuryl chloride on pyridine oxide , in: Ber. German Chem. Ges. , 1938 , 71 , pp. 2385-2388; doi : 10.1002 / cber.19380711126 .
↑ H. Yamanaka, T. Araki, T. Sakamoto: Site-Selectivity in the Reaction of 3-Substituted Pyridine 1-Oxides with Phosphoryl Chloride , in: Chem. Pharm. Bull. , 1988 , 36 , pp. 2244-2247, doi : 10.1248 / cpb.36.2244 , pdf .
↑ Y. Fort, S. Becker, P. Ca Clean: A convenient synthetic route to bis-heteroaromatic and bis-heterocyclic compounds promoted by liganded nickel complex reducing agents. , in: Tetrahedron , 1994 , 50 , pp. 11893-11902, doi : 10.1016 / S0040-4020 (01) 89303-0 .
↑ N. Kudo, M. Perseghini, GC Fu: A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles , in: Angew. Chem. , 2006 , 118 , pp. 1304-1304; doi : 10.1002 / anie.200503479 .

[king-1] H. King, LL Ware: 4 – Thiopyridone and derived substances , in: J. Chem. Soc. , 1939 , pp. 873-877; doi : 10.1039 / JR9390000873 .

[CRC-2] 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.

[3] CWN Cumper, AI Vogel: Physical properties and chemical constitution. Part XXX. The dipole moments of some halogeno- and cyano-pyridines , in: J. Chem. Soc. , 1960 , pp. 4723-4728; doi : 10.1039 / JR9600004723 .

[leis-4] A ^b D. G. Leis, B. Columba Curran: Electric Moments of Some γ-Substituted Pyridines , in: J. Am. Chem. Soc. , 1945 , 67 , pp. 79-81; doi : 10.1021 / ja01217a028 .

[NV-5] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[6] B. Bobranacuteski, L. Kochanacuteska, A. Kowalewska: On the action of sulfuryl chloride on pyridine oxide , in: Ber. German Chem. Ges. , 1938 , 71 , pp. 2385-2388; doi : 10.1002 / cber.19380711126 .

[7] H. Yamanaka, T. Araki, T. Sakamoto: Site-Selectivity in the Reaction of 3-Substituted Pyridine 1-Oxides with Phosphoryl Chloride , in: Chem. Pharm. Bull. , 1988 , 36 , pp. 2244-2247, doi : 10.1248 / cpb.36.2244 , pdf .

[8] Y. Fort, S. Becker, P. Ca Clean: A convenient synthetic route to bis-heteroaromatic and bis-heterocyclic compounds promoted by liganded nickel complex reducing agents. , in: Tetrahedron , 1994 , 50 , pp. 11893-11902, doi : 10.1016 / S0040-4020 (01) 89303-0 .

[9] N. Kudo, M. Perseghini, GC Fu: A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles , in: Angew. Chem. , 2006 , 118 , pp. 1304-1304; doi : 10.1002 / anie.200503479 .