2-vinylpyridine
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Preferred IUPAC name
2-Ethenylpyridine
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| Other names
2-Vinylpyridine
2VP |
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| Identifiers | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.002.618 |
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PubChem CID
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| Properties | |
| C7H7N | |
| Molar mass | 105.14 g·mol−1 |
| Appearance | Brown, clear liquid |
| Density | 0.977 g/cm3 |
| Melting point | −50 °C (−58 °F; 223 K) |
| Boiling point | 158 °C (316 °F; 431 K) |
| 27.5 g/L | |
| Vapor pressure | 96 hPa (72 mmHg) at 100 °C |
| Acidity (pKa) | 4.98 |
| Viscosity | 1.17 mPas |
| Hazards | |
| Flash point | 48 °C (118 °F; 321 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
2-Vinylpyridine is an organic compound with the formula CH2CHC5H4N. It is a derivative of pyridine with a vinyl group in the 2-position, next to the nitrogen. It is a colorless liquid although samples are often brown. It is used industrially as a precursor to specialty polymers and as an intermediate in the chemical, pharmaceutical, dye, and photo industries.
It was first synthesized in 1887. A contemporary preparation entails treatment of 2-methylpyridine with formaldehyde, followed by dehydration of the resulting intermediate alcohol. The reaction is carried out between 150–200 °C in an autoclave. The conversion must be kept relatively low with short reaction time to suppress the formation of byproducts. After removal of unreacted 2-methylpyridine by distillation, concentrated aqueous sodium hydroxide is added to the residue and the resultant mixture is distilled under reduced pressure. During distillation, the dehydration of 2-(2-pyridyl)ethanol occurs to give 2-vinylpyridine, which can be purified further by fractional distillation under reduced pressure in the presence of an inhibitor such as 4-tert-butylcatechol.
An alternative synthesis involves the reaction of acrylonitrile and acetylene below 130–140 ̊C in the presence of organocobalt compounds as a catalyst. Acrylonitrile is the solvent for the reaction.
Vinylpyridine is sensitive to polymerization. It may be stabilized with a free radical inhibitor such as tert-butylcatechol. Owing to its tendency to polymerize, samples are stored between 3-4 °C. It is incompatible with strong oxidizing agents, strong bases, strong acids.
2-Vinylpyridine is readily polymerized or copolymerized with styrene, butadiene, isobutylene, methyl methacrylate, and other compounds in the presence of radical, cationic, or anionic initiators. The homopolymer is soluble in organic solvents such as methanol and acetone, whereas cross-linked copolymers are insoluble in organic solvents.
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