Topic summary

Pyrrole

Pyrrole
Names Preferred IUPAC name
1H-Pyrrole
Other names
  • Azole
  • Imidole
Identifiers
3D model (JSmol)
1159 ChEBIChEMBLChemSpiderECHA InfoCard100.003.387EC Number
  • 203-724-7
1705 RTECS number
  • UX9275000
UNIIUN number1992, 1993
  • InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H
    Key: KAESVJOAVNADME-UHFFFAOYSA-N
  • InChI=1/C4H5N/c1-2-4-5-3-1/h1-5H
  • N1C=CC=C1
  • [nH]1cccc1
Properties C4H5NMolar mass67.091 g·mol Appearance colorless volatile liquid Density0.967 g cm Melting point−23 °C (−9 °F; 250 K) Boiling point129 to 131 °C (264 to 268 °F; 402 to 404 K) Vapor pressure7 mmHg at 23 °C Acidity (pKa) 17.5 (for the N−H proton) Basicity (pKb) 13.6 (pKa 0.4 for C.A.) −47.6×10 cm molViscosity0.001225 Pa s Thermochemistry 1.903 J K mol 108.2 kJ mol (gas) 2242 kJ mol Hazards NFPA 704 (fire diamond) Flash point33.33 °C (91.99 °F; 306.48 K) 550 °C (1,022 °F; 823 K) Explosive limits3.1–14.8% Safety data sheet (SDS) Chemical Safety DataRelated compounds
Related compounds
Phosphole, arsole, bismole, stibole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formulaC4H4NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.

Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls.