Structure via PubChem · Public domain (PubChem)
pyrrolidine
Sign in to saveAlso known as tetrahydropyrrole, tetramethylenimine, 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.
Chemical data
- Formula
- C4H9N
- Molecular weight
- 71.12 g/mol
- IUPAC name
- pyrrolidine
- SMILES
- C1CCNC1
- InChIKey
- RWRDLPDLKQPQOW-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Has part
- carbon
- Mass
- 71.073
Show 9 more facts
- boiling point
- 86.56
- found in taxon
- black pepper
- canonical SMILES
- C1CCNC1
- chemical formula
- C₄H₉N
- density
- 0.866
- Commons category
- Pyrrolidine
- pKa
- 11.27
- melting point
- -57.84
- ionization energy
- 8.00
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Production and synthesis
- Industrial production
- Laboratory synthesis
- Occurrence
- Reactions
- References
- External links
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.
==Production and synthesis== ===Industrial production=== Pyrrolidine is prepared industrially by the reaction of 1,4-butanediol and ammonia at a temperature of 165–200 °C and a pressure of 17–21 MPa in the presence of a cobalt- and nickel oxide catalyst, which is supported on alumina. 600px|upright=2.5|frameless|Reaction of 1,4-butanediol with ammonia to form pyrrolidine and water in the presence of a nickel oxide catalyst supported on alumina
Excerpted from Wikipedia’s “pyrrolidine” article, available under the CC BY-SA 4.0 licence.