4-Vinylpyridine

4-Vinylpyridine

Names
Preferred IUPAC name 4-Ethenylpyridine
Other names 4-VP
Identifiers
CAS Number	100-43-6
3D model (JSmol)	Interactive image
Beilstein Reference	104506
ChemSpider	7221
ECHA InfoCard	100.002.593
EC Number	202-852-0
PubChem CID	7502
UNII	I56G67XM8D
CompTox Dashboard (EPA)	DTXSID0051499
InChI InChI=1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2 Key: KFDVPJUYSDEJTH-UHFFFAOYSA-N
SMILES C=CC1=CC=NC=C1
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H314, H315, H317, H319, H330, H334, H411
Precautionary statements	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). Infobox references

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

• 2-Vinylpyridine

References

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   978-3-527-30673-2.
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.