pyrrole
Also known as monopyrrole, divinyleneimine, imidole, divinylenimine, 1-aza-2,4-cyclopentadiene, 1H-pyrrole, pyrrhol, azole
Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula . It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, . Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.
Chemical data
- Formula
- C4H5N
- Molecular weight
- 67.09 g/mol
- IUPAC name
- 1H-pyrrole
- SMILES
- C1=CNC=C1
- InChIKey
- KAESVJOAVNADME-UHFFFAOYSA-N
- XLogP
- 0.7
- Polar surface area
- 15.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Image
- Pyrrole Post Distillation.jpg
~14 min read
Article
21 sectionsContents
- Properties, structure, bonding
- History
- Occurrence in nature
- Synthesis
- Hantzsch pyrrole synthesis
- Knorr pyrrole synthesis
- Paal–Knorr pyrrole synthesis
- Other methods
- Biosynthesis
- Reactions and reactivity
- Reaction of pyrrole with electrophiles
- Acylation
- Reaction of deprotonated pyrrole
- Reductions
- Cyclization reactions
- Commercial uses
- Analogs and derivatives
- See also
- References
- Further reading
- External links
Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula . It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, . 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.