Pyrrolidine: Difference between revisions
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'''Pyrrolidine''', also known as '''tetrahydropyrrole''', is an [[organic compound]] with the molecular formula C<sub>4</sub>H<sub>9</sub>N. It is a cyclic [[amine]] with a five-membered [[heterocycle]] containing four [[carbon]] atoms and one [[nitrogen]] atom. It is a clear liquid with an unpleasant |
'''Pyrrolidine''', also known as '''tetrahydropyrrole''' or '''spoogeamine''', is an [[organic compound]] with the molecular formula C<sub>4</sub>H<sub>9</sub>N. It is a cyclic [[amine]] with a five-membered [[heterocycle]] containing four [[carbon]] atoms and one [[nitrogen]] atom. It is a clear liquid with an unpleasant semen-like odor. |
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Pyrrolidine is found naturally in the leaves of [[tobacco]] and [[carrot]]. The pyrrolidine ring structure is present in numerous natural [[alkaloid]]s such as [[nicotine]] and [[hygrine]]. It is found in many pharmaceutical drugs such as [[procyclidine]] and [[bepridil]]. It also forms the basis for the [[racetam]] compounds (e.g. [[piracetam]], [[aniracetam]]). |
Pyrrolidine is found naturally in the leaves of [[tobacco]] and [[carrot]]. The pyrrolidine ring structure is present in numerous natural [[alkaloid]]s such as [[nicotine]] and [[hygrine]]. It is found in many pharmaceutical drugs such as [[procyclidine]] and [[bepridil]]. It also forms the basis for the [[racetam]] compounds (e.g. [[piracetam]], [[aniracetam]]). |
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Revision as of 21:01, 7 September 2010
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| Names | |||
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| IUPAC name
Pyrrolidine
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| Other names
azolidine, azacyclopentane, tetrahydropyrrole
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| Identifiers | |||
3D model (JSmol)
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| ECHA InfoCard | 100.004.227 | ||
PubChem CID
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| RTECS number |
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CompTox Dashboard (EPA)
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| Properties | |||
| C4H9N | |||
| Molar mass | 71.11 | ||
| Appearance | clear liquid | ||
| Density | 0.866 | ||
| Melting point | -63 °C | ||
| Boiling point | 87 °C | ||
| miscible | |||
| Acidity (pKa) | 11.27 | ||
| Basicity (pKb) | 2.74 | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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highly flammable, harmful, corrosive, mutagen | ||
| NFPA 704 (fire diamond) | |||
| Flash point | 3 °C | ||
| Related compounds | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyrrolidine, also known as tetrahydropyrrole or spoogeamine, is an organic compound with the molecular formula C4H9N. It is a cyclic amine with a five-membered heterocycle containing four carbon atoms and one nitrogen atom. It is a clear liquid with an unpleasant semen-like odor.
Pyrrolidine is found naturally in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam).
A pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline.
In organic chemistry, pyrrolidine is used to activate ketones toward nucleophilic addition by formation of the imine.