Pyrrolidine

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Pyrrolidine
Pyrrolidine svg.svg
Pyrrolidine3d.png
Names
Preferred IUPAC name
Pyrrolidine
Other names
Azolidine
Azacyclopentane
Tetrahydropyrrole
Prolamine
Identifiers
  • 123-75-1 YesY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:33135 YesY
ChEMBL
  • ChEMBL22830 YesY
ChemSpider
  • 29008 YesY
ECHA InfoCard 100.004.227
PubChem CID
  • 31268
RTECS number UX9650000
UNII
  • LJU5627FYV YesY
Properties
C4H9N
Molar mass 71.12 g·mol−1
Appearance Clear colorless liquid
Density 0.866 g/cm3
Melting point −63 °C (−81 °F; 210 K)
Boiling point 87 °C (189 °F; 360 K)
Miscible
Acidity (pKa) 11.27 (pKa of conjugate acid in water),[1]

19.56 (pKa of conjugate acid in acetonitrile)[2]

-54.8·10−6 cm3/mol
Hazards
Main hazards highly flammable, harmful, corrosive, possible mutagen
Safety data sheet MSDS
R-phrases (outdated) R11-R20/21/22-R34[3]
S-phrases (outdated) S16-S26-S28-S36/37-S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 3 °C (37 °F; 276 K)
345 °C (653 °F; 618 K)
Related compounds
Related nitrogen heterocyclic compounds
Pyrrole (aromatic with two double bonds)
Pyrroline (one double bond)
Pyrrolizidine (two pentagonal rings)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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".[4] In addition to pyrrolidine itself, many substituted pyrrolidines are known.

Synthesis and occurrence

Pyrrolidine is produced by treatment of 1,4-butanediol with ammonia over an oxide catalyst.[5]

Many modifications of pyrrolidine are found in natural and synthetic chemistry. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). The amino acids proline and hydroxyproline are, in a structural sense, derivatives of pyrrolidine.

Nicotine contains an N-methylpyrrolidine ring linked to a pyridine ring.

Reactions

Pyrrolidine is a base. Its basicity is typical of other dialkyl amines.[6] Relative to many secondary amines, pyrrolidine is distinctive because of its compactness, a consequence of its cyclic structure.

Pyrrolidine is used as a building block in the synthesis of more complex organic compounds. It is used to activate ketones and aldehydes toward nucleophilic addition by formation of enamines:[7]

Enamine.png

References

  1. ^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society. 79 (20): 5441–5444. doi:10.1021/ja01577a030. 
  2. ^ Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". The Journal of Organic Chemistry. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863. 
  3. ^ MSDS
  4. ^ Pyrrolidine, The Good Scents Company
  5. ^ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
  6. ^ H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441. doi:10.1021/ja01577a030. 
  7. ^ R. B. Woodward, I. J. Pachter, and M. L. Scheinbaum (1974). "2,2-(Trimethylenedithio)cyclohexanone". Organic Syntheses. 54: 39.  ; Collective Volume, 6, p. 1014 

External links

  • Media related to Pyrrolidine at Wikimedia Commons
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