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2-Bromopyridine

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2-Bromopyridine
Names
Preferred IUPAC name 2-Bromopyridine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.311 Edit this at Wikidata
EC Number
  • 203-641-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4HKey: IMRWILPUOVGIMU-UHFFFAOYSA-N
  • InChI=1/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4HKey: 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 , 100 kPa). Infobox references
Chemical compound

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

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

  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. 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.
  3. 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
  4. 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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