Pyrrolidine
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| Names | |||
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| IUPAC name
Pyrrolidine
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| Other names
Azolidine
Azacyclopentane Tetrahydropyrrole Prolamine |
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| Identifiers | |||
123-75-1  |
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| ChEBI | CHEBI:33135 |
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| ChEMBL | ChEMBL22830 |
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| ChemSpider | 29008 |
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| Jmol 3D model | Interactive image | ||
| PubChem | 31268 | ||
| RTECS number | UX9650000 | ||
| UNII | LJU5627FYV |
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| Properties | |||
| C4H9N | |||
| Molar mass | 71.12 g·mol−1 | ||
| Appearance | Clear colorless liquid | ||
| Density | 0.866 g/cm3 | ||
| Melting point | −63 °C (−81 °F; 210 K) | ||
| Boiling point | 87 °C (189 °F; 360 K) | ||
| Miscible | |||
| Acidity (pKa) | 11.27 (pKa of conjugate acid in water),[1] 19.56 (pKa of conjugate acid in acetonitrile)[2] |
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| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related Nitrogen heterocyclic compounds
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Pyrrole (aromatic with two double bonds) Pyrroline (one double bond) Pyrrolizidine (two pentagonal rings) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH2)4NH. It is a cyclic secondary amine, also classified as a saturated heterocycle. It is a colourless liquid that is miscible with water and most organic solvents. It has a characteristic semen-like odor.[3] Compared to acyclic secondary amines, it is about 10 times more basic.
Synthesis and occurrence
Pyrrolidine is produced industrially by treatment of 1,4-butanediol with ammonia over an oxide catalyst.[4]
Pyrrolidine is found 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). The amino acids proline and hydroxyproline are, in a structural sense, derivatives of pyrrolidine.
Applications
Pyrrolidine is used as a building block in the synthesis of more complex compounds. In organic chemistry, pyrrolidine is used to activate ketones and aldehydes toward nucleophilic addition by formation of enamines:[5]
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
