Pyrrolidine

Pyrrolidine
IUPAC name	Pyrrolidine
Other names	azolidine, azacyclopentane, tetrahydropyrrole
Identifiers
CAS number	123-75-1 Y
PubChem	31268
RTECS number	UX9650000
SMILES	C1CCNC1
Properties
Molecular formula	C4H9N
Molar mass	71.11
Appearance	clear liquid
Density	0.866
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	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)
Y (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 ring 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.

External links

• Pyrrolidine MSDS