4-Vinylpyridine (4-VP) is an organic compound with the formula CH2CHC5H4N. It is a derivative of pyridine with a vinyl group in the 4-position. It is a colorless liquid, although impure samples are often brown. It is a monomeric precursor to specialty polymers. 4-Vinylpyridine is prepared by the condensation of 4-methylpyridine and formaldehyde.[1]
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| Names | |
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| Preferred IUPAC name
4-Ethenylpyridine | |
| Other names
4-VP | |
| Identifiers | |
3D model (JSmol) |
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| 104506 | |
| ChemSpider | |
| ECHA InfoCard | 100.002.593 
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| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H7N | |
| Molar mass | 105.140 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.988 g/cm3 |
| Boiling point | 62–65 °C (144–149 °F; 335–338 K) 15 mmHg |
| Hazards | |
| GHS labelling: | |
     
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| Danger | |
| H226, H301, H314, H315, H317, H319, H330, H334, H411 | |
| P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P284, P285, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P320, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4-VP is sometimes used in biochemistry to alkylate protein cysteine residues. When compared to other alkylation agents, such as iodoacetamide, acrylamide, and N-ethylmaleimide, 4-VP is less reactive, meaning the completion rate of cysteine alkylation is lower, but it also yields fewer side reactions.[2] For some uses, such as during mass spectrometry measurements, 4-VP might be better because it is basic and can thus be protonated, adding net charge.[3]