Pyrrolidine

Chembox new
ImageFileL1=Pyrrolidine.pngImageSizeL1=80px
ImageFileR1=Pyrrolidine3d.pngImageSizeR1=100px
IUPACName=Pyrrolidine
OtherNames=azolidine, azacyclopentane, tetrahydropyrrole
Section1= Chembox Identifiers
CASNo=123-75-1
PubChem=31268
SMILES=C1CCNC1
RTECS=UX9650000
Section2= Chembox Properties
Formula=C₄H₉N
MolarMass=71.11
Appearance=clear liquid
Density=0.866
MeltingPt=-63 °C
BoilingPt=87 °C
Solubility=miscible
pKa = 11.27
pKb = 2.74
Section3= Chembox Hazards
MainHazards=highly flammable, harmful, corrosive, mutagen
FlashPt=3 °C
Autoignition = 345 °C
NFPA-H = 3
NFPA-F = 3
NFPA-R = 1
RPhrases=11 20/21/22 35
SPhrases=16 26 28 36/37 45
Section8 = Chembox Related
OtherCpds = pyrrole piperidine

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.

See also

* Pyrrole, the aromatic analog with two double bonds
* Pyrroline, an analog with one double bond

External links

* [https://fscimage.fishersci.com/msds/96268.htm Pyrrolidine MSDS]