2-Bromopyridine

2-Bromopyridine
Names
	Preferred IUPAC name 2-Bromopyridine
Identifiers
CAS Number	109-04-6 ;
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 ;
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
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.^[1]

Reactions

2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine,^[2] which is a versatile reagent.^[3] 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.^[4]

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

^ Allen, C. F. H.; Thirtle, John R. "2-Bromopyridine" Organic Syntheses 1946, volume 26, pp. 16-18. doi:10.15227/orgsyn.026.0016
^ Yamamoto, Yasunori; Sugai, Juugaku; Takizawa, Miho; Miyaura, Norio (2011). "Synthesis of Lithium 2-Pyridyltriolborate and ITS Cross-Coupling Reaction with Aryl Halides". Organic Syntheses. 88: 79. doi:10.15227/orgsyn.088.0079.
^ 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
^ Knight, David W.; Hartung, Jens (15 September 2006). "1-Hydroxypyridine-2(1H)-thione". 1-Hydroxypyridine-2(1H)-thione. Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rh067.pub2. ISBN 0471936235.