2-Bromopyridine

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2-Bromopyridine
2-Brpyridine.png
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Names
Preferred IUPAC name
2-Bromopyridine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.311 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-641-6
PubChem CID
UNII
  • 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
  • c1ccnc(c1)Br
Properties
C5H4NBr
Molar mass 158.00
Appearancecolorless liquid
Boiling point 194.8 °C
Acidity (pKa)0.71 (for C5H4(Br)NH+) [1]
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).

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. [2]

Contents

Reactions

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

2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine, [3] which is a versatile reagent. [4] 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. [5]

Applications

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

References

  1. ↑ Linnell, Robert (1960). "Notes- Dissociation Constants of 2-Substituted Pyridines". The Journal of Organic Chemistry. 25 (2): 290. doi:10.1021/jo01072a623.
  2. ↑ Allen, C. F. H.; Thirtle, John R. "2-Bromopyridine" Organic Syntheses 1946, volume 26, pp. 16-18. doi : 10.15227/orgsyn.026.0016
  3. ↑ 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 .
  4. ↑ 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
  5. ↑ 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.
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