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83240 Sigma-Aldrich

Pyrrolidine

puriss. p.a., ≥99.0%

Synonym: Tetrahydropyrrole, Tetramethyleneimine

  • CAS Number 123-75-1

  • Empirical Formula (Hill Notation) C4H9N

  • Molecular Weight 71.12

  •  Beilstein/REAXYS Number 102395

  •  EC Number 204-648-7

  •  MDL number MFCD00005249

  •  PubChem Substance ID 329769283

  •  NACRES NA.22

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Properties

Related Categories Analytical Reagents, Analytical Reagents for General Use, Analytical/Chromatography, Building Blocks, C4 to C8,
Quality Level   100
vapor density   2.45 (vs air)
vapor pressure   128 mmHg ( 39 °C)
  49 mmHg ( 20 °C)
grade   puriss. p.a.
assay   ≥99.0% (GC)
  ≥99.0%
autoignition temp.   653 °F
expl. lim.   10.6 %
impurities   ≤0.5% water
refractive index   n20/D 1.443 (lit.)
  n20/D 1.443
bp   87-88 °C/760 mmHg (lit.)
density   0.852 g/mL at 25 °C (lit.)
cation traces   Al: ≤0.5 mg/kg
  Ba: ≤0.1 mg/kg
  Bi: ≤0.1 mg/kg
  Ca: ≤0.5 mg/kg
  Cd: ≤0.05 mg/kg
  Co: ≤0.02 mg/kg
  Cr: ≤0.02 mg/kg
  Cu: ≤0.02 mg/kg
  Fe: ≤0.1 mg/kg
  K: ≤0.5 mg/kg
  Li: ≤0.1 mg/kg
  Mg: ≤0.1 mg/kg
  Mn: ≤0.02 mg/kg
  Mo: ≤0.1 mg/kg
  Na: ≤0.5 mg/kg
  Ni: ≤0.02 mg/kg
  Pb: ≤0.1 mg/kg
  Sr: ≤0.1 mg/kg
  Zn: ≤0.1 mg/kg
SMILES string   C1CCNC1
InChI   1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
InChI key   RWRDLPDLKQPQOW-UHFFFAOYSA-N

Description

Application

Pyrrolidine can be used as:
• A base for the chemoselective reduction of ketones to alcohol in the presence of decaborane and cerium(III) chloride heptahydrate in methanol.
• A reactant with benzaldehyde and β-naphthol for the synthesis of betti base using non-ionic surfactant (Triton X-100) as a catalyst.
• A catalyst in the synthesis of aldimines from aldehydes and primary amines.
• A modifier for aluminum hydride reagent, which is used as a selective reducing agent to transform N-benzyl-4-ethoxycarbonylpiperidine into N-benzyl-4-formylpiperidine.
• As a solvent/base in palladium-catalyzed Sonagashira coupling reactions.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 1922 8(3) / PGII
WGK Germany 
WGK 1
RTECS 
UX9650000
Flash Point(F) 
37.4 °F - closed cup
Flash Point(C) 
3 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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