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 odor that has been described as "ammoniacal, fishy, shellfish-like". In addition to pyrrolidine itself, many substituted pyrrolidines are known.
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Pyrrolidine
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| Other names
Azolidine
Azacyclopentane Tetrahydropyrrole Prolamine | |||
| 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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| -54.8·10−6 cm3/mol | |
| Hazards | |
| Main hazards | highly flammable, harmful, corrosive, possible mutagen |
| Safety data sheet | MSDS |
| R-phrases(outdated) | R11-R20/21/22-R34[3] |
| S-phrases(outdated) | S16-S26-S28-S36/37-S45 |
| NFPA 704 | |
| Flash point | 3 °C (37 °F; 276 K) |
| 345 °C (653 °F; 618 K) | |
| Related compounds | |
Related nitrogen heterocyclic compounds
| Pyrrole (aromatic with two double bonds) Pyrroline (one double bond) Pyrrolizidine (two pentagonal rings) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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