Pyrrolidine;Prolamine;Azolidine

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

Properties
Chemical formula	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)
Solubility in water	Miscible
Acidity (pKa)	11.27 (pKa of conjugate acid in water),[1] 19.56 (pKa of conjugate acid in acetonitrile)[2]
Magnetic susceptibility (χ)	-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R-phrases(outdated)	R11-R20/21/22-R34[3]
S-phrases(outdated)	S16-S26-S28-S36/37-S45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	3 3 1
Flash point	3 °C (37 °F; 276 K)
Autoignition temperature	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).