2,6-dibromopyridine

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Structural formula
Structural formula of 2,6-dibromopyridine
General
Surname 2,6-dibromopyridine
Molecular formula C 5 H 3 Br 2 N
Brief description

beige solid

External identifiers / databases
CAS number 626-05-1
EC number 210-926-9
ECHA InfoCard 100.009.934
PubChem 12274
Wikidata Q209274
properties
Molar mass 236,90 g · mol -1
Physical state

firmly

Melting point

116-119 ° C

solubility

practically insoluble in water

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 300-315-319-412
P: 273-302 + 352-305 + 351 + 338-309 + 310
Toxicological data

31 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 .

2,6-Dibromopyridine is an organic compound that belongs to the heterocycles (more precisely: heteroaromatic compounds ). It consists of a pyridine ring which is substituted with bromine in the 2- and 6-positions .

presentation

2,6-dibromopyridine, by reaction of pyridine N oxide with tert -butyllithium and carbon tetrabromide are prepared. It is also obtained as a by-product in the synthesis of 2-bromopyridine with bromine at 500 ° C.

use

By reaction of 2-bromopyridine and 2,6-dibromopyridine with copper in the sense of an Ullmann coupling can terpyridine be prepared.

The synthesis of 3-nitropyridine is possible by reacting 2,6-dibromopyridine with nitronium tetrafluoroborate and subsequent dehalogenation.

Individual evidence

  1. ↑ a b c d e f data sheet 2,6-dibromopyridine (PDF) from Merck , accessed on December 25, 2019.
  2. ↑ I. Popov, H.-Q. Do, O. Daugulis: In Situ Generation and Trapping of Aryllithium and Arylpotassium Species by Halogen, Sulfur, and Carbon Electrophiles , in: J. Org. Chem. , 2009 , 74 , pp. 8309-8313; doi : 10.1021 / jo9015369 .
  3. ↑ SM McElvain, MA Goese: The Halogenation of Pyridine , in: J. Am. Chem. Soc. , 1943 , 65 , pp. 2227-2233; doi : 10.1021 / ja01251a062 .
  4. ^ FH Burstall: Researches on the polypyridyls , in: J. Chem. Soc. , 1938 , pp. 1662-1672; doi : 10.1039 / JR9380001662 .
  5. ↑ Joseph L. Duffy, Kenneth K. Laali: "Aprotic Nitration (NO 2 + BF 4 - ) of 2-Halo- and 2,6-Dihalopyridines and Transfer-Nitration Chemistry of Their N -Nitropyridinium Cations", in: J. Org. Chem. , 1991 , 56 , pp. 3006-3009; doi : 10.1021 / jo00009a015 .