2-Bromopyridine

2-Bromopyridine

Names
Preferred IUPAC name 2-Bromopyridine
Identifiers
CAS Number	109-04-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:51574
ChEMBL	ChEMBL331374
ChemSpider	7685
ECHA InfoCard	100.003.311
EC Number	203-641-6
PubChem CID	7973
UNII	7Z7MLC4VD8 Y
CompTox Dashboard (EPA)	DTXSID6051564
InChI InChI=1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H Key: IMRWILPUOVGIMU-UHFFFAOYSA-N InChI=1/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H Key: IMRWILPUOVGIMU-UHFFFAOYAP
SMILES c1ccnc(c1)Br
Properties
Chemical formula	C5H4NBr
Molar mass	158.00
Appearance	colorless liquid
Boiling point	194.8 °C
Acidity (pKa)	0.71 (for C5H4(Br)NH+)
Related compounds
Related compounds	2-Chloropyridine 3-Bromopyridine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Bromopyridine is an aryl bromide and isomer of bromopyridine with the formula BrC₅H₄N. It is a colorless liquid that is used as an intermediate in organic synthesis. It can be prepared from 2-aminopyridine via diazotization followed by bromination.

Reactions

Like 2-chloropyridine, 2-bromopyridine is very weakly basic.

2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine, which is a versatile reagent. Pyrithione can be prepared in a two-step synthesis from 2-bromopyridine by oxidation to the N-oxide with a suitable peracid followed by substitution using either sodium dithionite or sodium sulfide with sodium hydroxide to introduce the thiol functional group.

Applications

Organometallic addition to benzophenone followed by catalytic hydrogenation is the synthesis of pipradrol.

References