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Pyrrolidine
Pyrrolidine.png
Pyrrolidine3d.png
IUPAC name
Other names azolidine, azacyclopentane, tetrahydropyrrole
Identifiers
CAS number 123-75-1 Yes check.svgY
PubChem 31268
RTECS number UX9650000
SMILES
Properties
Molecular formula C4H9N
Molar mass 71.11
Appearance clear liquid
Density 0.806
Melting point

-63 °C

Boiling point

87 °C

Solubility in water miscible
Acidity (pKa) 11.27
Basicity (pKb) 2.74
Hazards
R-phrases 11 20/21/22 35
S-phrases 16 26 28 36/37 45
NFPA 704
NFPA 704.svg
3
3
1
 
Flash point 3 °C
Autoignition
temperature
345 °C
Related compounds
Related Nitrogen heterocyclic compounds Pyrrole (aromatic with two double bonds)
Pyrroline (one double bond)
Pyrrolizidine (two pentagonal rings)
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula C4H9N. It is a cyclic amine with a five-membered heterocycle containing four carbon atoms and one nitrogen atom. It is a clear liquid with an unpleasant ammonia-like odor.

Pyrrolidine is found naturally in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam).

A pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline.

In organic chemistry, pyrrolidine is used to activate ketones toward nucleophilic addition by formation of the imine.

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