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.
Pyrrolidine
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| Names |
| Preferred IUPAC name
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| Other names
Azolidine
Azacyclopentane
Tetrahydropyrrole
Prolamine
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| Properties |
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Chemical formula
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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) |
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Solubility in water
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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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Magnetic susceptibility (χ)
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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| R-phrases(outdated) |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| S-phrases(outdated) |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 |
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| Flash point |
3 °C (37 °F; 276 K) |
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|
345 °C (653 °F; 618 K) |
| 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) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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China
