2-Bromopyridine
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Preferred IUPAC name
2-Bromopyridine | |||
| Identifiers | |||
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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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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.