| Pyrrolidine | |
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Pyrrolidine |
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Other names
azolidine, azacyclopentane, tetrahydropyrrole, spoogeamine |
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| Identifiers | |
| CAS number | 123-75-1 |
| PubChem | 31268 |
| ChemSpider | 29008 |
| UNII | LJU5627FYV |
| ChEBI | CHEBI:33135 |
| ChEMBL | CHEMBL22830 |
| RTECS number | UX9650000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H9N |
| Molar mass | 71.12 g mol−1 |
| Appearance | Clear liquid |
| Density | 0.866 g/cm3 |
| Melting point |
-63 °C, 210 K, -81 °F |
| Boiling point |
87 °C, 360 K, 189 °F |
| Solubility in water | Miscible |
| Acidity (pKa) | 11.27 (pKa of conjugate acid in water),[1] 19.56 (pKa of conjugate acid in acetonitrile)[2] |
| Hazards | |
| R-phrases | R11 R20/21/22 R35 |
| S-phrases | S16 S26 S28 S36/37 S45 |
| Main hazards | highly flammable, harmful, corrosive, mutagen |
| NFPA 704 |
3
3
1
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| Flash point | 3 °C |
| Autoignition temperature |
345 °C |
| Related compounds | |
| Related Nitrogen heterocyclic compounds | Pyrrole (aromatic with two double bonds) Pyrroline (one double bond) Pyrrolizidine (two pentagonal rings) |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula C4H9N. It is a cyclic secondary amine with a five-membered heterocycle containing four carbon atoms and one nitrogen atom. It is a clear liquid with an unpleasant odor that is ammoniacal, fishy, shellfish-like and very semen-like.[3]
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.
Pyrrolidine is a strong base and is by its basicity one of the strongest simple amines known.
In organic chemistry, pyrrolidine is used to activate ketones and aldehydes toward nucleophilic addition by formation of the iminium. It can also promote the aldol condensation of ketones and aldehydes by formation of the enamine.