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|ImageFileL1=Pyrrolidine.png
{{WikiProjectBannerShell|1=
|ImageSizeL1=80px
{{WikiProject Ships
|ImageFileR1=Pyrrolidine3d.png
|nested = yes
|ImageSizeR1=100px
|class = Disambig
|IUPACName=Pyrrolidine
|importance = NA }}
|OtherNames=azolidine, azacyclopentane, tetrahydropyrrole
{{WPMILHIST
|Section1= {{Chembox Identifiers
|nested = yes
| CASNo=123-75-1
|class = Dab
| PubChem=31268
|Maritime-task-force = yes
| SMILES=C1CCNC1
|German-task-force = yes }}
| RTECS=UX9650000
{{WikiProject Germany
}}
|nested = yes
|Section2= {{Chembox Properties
|class = Disambig
| Formula=C<sub>4</sub>H<sub>9</sub>N
|importance = NA }}
| 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 C<sub>4</sub>H<sub>9</sub>N. 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 [[alkaloid]]s 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 acid]]s [[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]

[[Category:Pyrrolidines| ]]
[[Category:Amines]]
[[Category:Solvents]]

[[de:Pyrrolidin]]
[[lv:Pirolidīns]]
[[ja:ピロリジン]]
[[pl:Pirolidyna]]
[[pt:Pirrolidina]]
[[ru:Пирролидин]]
[[sv:Pyrrolidin]]

Revision as of 14:45, 10 October 2008

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