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Topic summary

Pyrrolidine

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Names Preferred IUPAC name
Pyrrolidine
Other names
Azolidine
Azacyclopentane
Tetrahydropyrrole
Prolamine
Azolane
Identifiers
3D model (JSmol)
102395 ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.004.227EC Number
  • 204-648-7
1704
RTECS number
  • UX9650000
UNII
UN number1922
  • InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
    Key: RWRDLPDLKQPQOW-UHFFFAOYSA-N
  • InChI=1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
    Key: RWRDLPDLKQPQOW-UHFFFAOYAX
  • C1CCNC1
Properties C4H9NMolar mass71.123 g·mol Appearance Clear colorless liquid Density0.866 g/cm Melting point−63 °C (−81 °F; 210 K) Boiling point87 °C (189 °F; 360 K) Miscible Acidity (pKa) 11.27 (pKa of conjugate acid in water),

19.56 (pKa of conjugate acid in acetonitrile)

−54.8·10 cm/mol 1.4402 at 28°C Hazards Occupational safety and health (OHS/OSH):
Main hazards
highly flammable, harmful, corrosive, possible mutagen GHS labelling: DangerH225, H302, H314, H332P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P235, P405, P501NFPA 704 (fire diamond)
3
3
1
Flash point3 °C (37 °F; 276 K) 345 °C (653 °F; 618 K) Safety data sheet (SDS) MSDSRelated 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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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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