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4-Vinylpyridine
Names
Preferred IUPAC name
4-Ethenylpyridine
Other names
4-VP
Identifiers
3D model (JSmol)
104506
ChemSpider
ECHA InfoCard 100.002.593 Edit this at Wikidata
EC Number
  • 202-852-0
UNII
  • InChI=1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2
    Key: KFDVPJUYSDEJTH-UHFFFAOYSA-N
  • C=CC1=CC=NC=C1
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:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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).

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]

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]

See also[edit]

References[edit]

  1. ^ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
  2. ^ Suttapitugsakul, Suttipong; Xiao, Haopeng; Smeekens, Johanna; Wu, Ronghu (2017). "Evaluation and optimization of reduction and alkylation methods to maximize peptide identification with MS-based proteomics". Molecular BioSystems. 13 (12): 2574–2582. doi:10.1039/C7MB00393E. ISSN 1742-206X. PMC 5698164. PMID 29019370.
  3. ^ Sechi, Salvatore; Chait, Brian T. (1998-12-01). "Modification of Cysteine Residues by Alkylation. A Tool in Peptide Mapping and Protein Identification". Analytical Chemistry. 70 (24): 5150–5158. doi:10.1021/ac9806005. ISSN 0003-2700. PMID 9868912.
source: https://en.wikipedia.org/wiki/4-Vinylpyridine