File:Pyridine-2D-full.svg · Wikimedia Commons · See Wikimedia Commons
pyridine
Sign in to saveAlso known as azabenzene, py, Tritisan, pyridin, piridina
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow. The pyridine ring occurs in many commercial compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide.
Pyridine is a colorless liquid chemical compound similar to benzene but with a nitrogen atom in its ring structure, known for its flammable nature and distinctive fishy smell. It's an important ingredient in thousands of commercial products including pesticides, medicines, and vitamins, with about 20,000 tons produced globally each year.
AI-generated from the Wikipedia summary — may contain errors.
Chemical data
- Formula
- C5H5N
- Molecular weight
- 79.1 g/mol
- IUPAC name
- pyridine
- SMILES
- C1=CC=NC=C1
- InChIKey
- JUJWROOIHBZHMG-UHFFFAOYSA-N
- XLogP
- 0.7
- Polar surface area
- 12.9 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 79.042
- Image
- Pyridine sample.jpg
Show 17 more facts
- MCN code
- 2933.31.10
- Commons category
- Pyridine
- chemical formula
- C₅H₅N
- upper flammable limit
- 12.4
- flash point
- 68
- lower flammable limit
- 1.8
- NIOSH Pocket Guide ID
- 0541
- density
- 0.98
- immediately dangerous to life or health
- 3240
- melting point
- -41.66
- boiling point
- 115.23
- vapor pressure
- 16
- ionization energy
- 9.25
- time-weighted average exposure limit
- 15
- canonical SMILES
- C1=CC=NC=C1
- dynamic viscosity
- 0.94
- electric dipole moment
- 2.215
Sources (8)
via Wikidata · CC0
~30 min read
Article
36 sectionsContents
- Properties
- Physical properties
- Structure
- Spectroscopy
- Bonding
- History
- Occurrence
- In foods
- Production
- Chichibabin synthesis
- Dealkylation and decarboxylation of substituted pyridines
- Bönnemann cyclization
- Other methods
- Biosynthesis
- Reactions
- Electrophilic substitutions
- Nucleophilic substitutions
- Radical reactions
- Reactions on the nitrogen atom
- Hydrogenation and reduction
- Lewis basicity and coordination compounds
- Applications
- Pesticides and pharmaceuticals
- Laboratory use
- Reagents
- Hazards
- Fire
- Short-term exposure
- Long-term exposure
- Metabolism
- Environmental fate
- Nomenclature
- See also
- References
- Bibliography
- External links
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow. The pyridine ring occurs in many commercial compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide.
==Properties== class=skin-invert-image|thumb|142px|left|Internal bond angles and bond distances (in picometer|pm) for pyridine.