Pyrrolidine

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
Names
Preferred IUPAC name
Pyrrolidine
Other names
Azolidine
Azacyclopentane
Tetrahydropyrrole
Prolamine
Azolane
Identifiers
3D model (JSmol)
102395
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.227
EC Number
  • 204-648-7
1704
RTECS number
  • UX9650000
UNII
UN number 1922
  • InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 Y
    Key: RWRDLPDLKQPQOW-UHFFFAOYSA-N Y
  • InChI=1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
    Key: RWRDLPDLKQPQOW-UHFFFAOYAX
  • C1CCNC1
Properties
C4H9N
Molar mass 71.123 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),

19.56 (pKa of conjugate acid in acetonitrile)

-54.8·10−6 cm3/mol
1.4402 at 28°C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
highly flammable, harmful, corrosive, possible mutagen
GHS labelling:
Danger
H225, H302, H314, H332
P210, P233, P240, P241, P242, P243, P260, P261, 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, P501
NFPA 704 (fire diamond)
3
3
1
Flash point 3 °C (37 °F; 276 K)
345 °C (653 °F; 618 K)
Safety data sheet (SDS) MSDS
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).
Y verify (what is YN ?)
Infobox references
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