3-bromopyridine

Structural formula
General
Surname	3-bromopyridine
other names	m -bromopyridine; meta -bromopyridine;
Molecular formula	C 5 H 4 BrN
Brief description	yellowish liquid with a pyridine-like odor
External identifiers / databases
EC number	210-952-0
ECHA InfoCard	100.009.957
PubChem	12286
Wikidata	Q223057
properties
Molar mass	158.00 g mol −1
Physical state	liquid
density	1.62 g cm −3 (20 ° C)
Melting point	−27.3 ° C
boiling point	173 ° C
Vapor pressure	2.33 h Pa (25 ° C)
solubility	moderate in water (31 g l −1 at 25 ° C)
Refractive index	1.5694 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 302 + 352-304 + 340-305 + 351 + 338
	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

3-Bromopyridine is an organic compound that belongs to the heterocycles (more precisely: heteroaromatic compounds ). It consists of a pyridine ring which is substituted in the 3-position with bromine .

Manufacturing

3-Bromopyridine can be made by reacting pyridine with bromine and fuming sulfuric acid. In sulfuric acid, however, there is no reaction, which is why it is discussed that sulfur trioxide , which is contained in fuming sulfuric acid, is required to activate pyridine .

use

Like most brominated pyridine derivatives , 3-bromopyridine can also be used to produce other pyridine derivatives that are not directly accessible. The organolithium compound , accessible by halogen metal exchange with n -butyllithium , can be reacted as a nucleophile with electrophiles . It can be used in palladium- catalyzed reactions such as Heck reaction , Stille coupling or Sonogashira coupling .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet 3-bromopyridine (PDF) from Merck , accessed on June 23, 2011.
↑ ^a ^b ^c 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. 3-70.
^ ^A ^b J. A. Joules, K. Mills: Heterocyclic Chemistry , 2000 , 4th edition, Blackwell Science, Oxford, ISBN 0-632-05453-0 , pp. 77-81.

[merck-1] ↑ ^a ^b ^c ^d ^e ^f data sheet 3-bromopyridine (PDF) from Merck , accessed on June 23, 2011.

[CRC90_3_70-2] 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. 3-70.

[joules-3] A ^b J. A. Joules, K. Mills: Heterocyclic Chemistry , 2000 , 4th edition, Blackwell Science, Oxford, ISBN 0-632-05453-0 , pp. 77-81.