2-Bromopyridine
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| Preferred IUPAC name
2-Bromopyridine | |||
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| ECHA InfoCard | 100.003.311 | ||
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| Properties | |||
| C5H4NBr | |||
| Molar mass | 158.00 | ||
| Appearance | colorless 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).
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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]
Reactions
[edit]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
[edit]Organometallic addition to benzophenone followed by catalytic hydrogenation is the synthesis of pipradrol.
References
[edit]- ↑ Linnell, Robert (1960). "Notes- Dissociation Constants of 2-Substituted Pyridines". The Journal of Organic Chemistry. 25 (2): 290. doi:10.1021/jo01072a623.
- ↑ Allen, C. F. H.; Thirtle, John R. "2-Bromopyridine" Organic Syntheses 1946, volume 26, pp. 16-18. doi:10.15227/orgsyn.026.0016
{{doi}}: unflagged free DOI (link) - ↑ 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.