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
ChemSpider	7685
EC Number	203-641-6
PubChem CID	7973
UNII	7Z7MLC4VD8 Y
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
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 organic compound 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.^[1] It reacts with butyllithium to give 2-lithiopyridine, a versatile reagent.^[2] 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.^[3]

References

1. ↑ Allen, C. F. H.; Thirtle, John R. "2-Bromopyridine" Organic Syntheses 1946, volume 26, pp. 16-18. doi:10.15227/orgsyn.026.0016
2. ↑ Satinder V. Kessar, Paramjit Singh, Dmitry Zuev, Zhenlei Song, Ya Wu "2-Lithiopyridine" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2015. doi:10.1002/047084289X.rl025.pub3
3. ↑ Knight, David W.; Hartung, Jens (15 September 2006). "1-Hydroxypyridine-2(1H)-thione". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rh067.pub2.  |access-date= requires |url= (help)