Date published: 2025-10-14

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2-Vinylpyridine (CAS 100-69-6)

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Alternate Names:
2-Ethenylpyridine; α-Vinylpyridine
Application:
2-Vinylpyridine is a reagent for pyridylethylation
CAS Number:
100-69-6
Purity:
≥97%
Molecular Weight:
105.14
Molecular Formula:
C7H7N
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-Vinylpyridine (2-VP) is an organic compound presenting as a colorless liquid with a subtle sweet scent. 2-Vinylpyridine holds a prominent position, owing to its broad range of applications. It acts as a precursor for synthesizing various heterocyclic compounds like pyridines and pyrroles. 2-Vinylpyridine (2-VP) serves as a vital component in polymer synthesis, with polyvinylpyridine, derived from 2-Vinylpyridine, finding application in materials science. Within biochemistry, 2-Vinylpyridine assumes the role of a substrate for synthesizing diverse enzymes, including cytochrome P450, and functions as a ligand for binding metal ions. The reactivity of 2-Vinylpyridine stems from its characteristics as a weak base and nucleophile, which are contingent upon the solution′s pH. Lower pH levels enhance its reactivity, enabling the formation of covalent bonds with other molecules. Conversely, at higher pH levels, its reactivity diminishes, leading to the formation of hydrogen bonds with other molecules.


2-Vinylpyridine (CAS 100-69-6) References

  1. C-H bond activation and subsequent C-C bond formation promoted by osmium: 2-vinylpyridine-acetylene couplings.  |  Esteruelas, MA., et al. 2006. J Am Chem Soc. 128: 4596-7. PMID: 16594696
  2. Metal coordination by sterically hindered heterocyclic ligands, including 2-vinylpyridine, assessed by investigation of cobaloximes.  |  Siega, P., et al. 2006. Inorg Chem. 45: 3359-68. PMID: 16602795
  3. Isotope-coded two-dimensional maps: tagging with deuterated acrylamide and 2-vinylpyridine.  |  Righetti, PG., et al. 2008. Methods Mol Biol. 424: 87-99. PMID: 18369855
  4. Cobalt-catalyzed addition of styrylboronic acids to 2-vinylpyridine derivatives.  |  Kobayashi, T., et al. 2011. Chem Asian J. 6: 669-73. PMID: 20665650
  5. A new access to 4 H-quinolizines from 2-vinylpyridine and alkynes promoted by rhodium-N-heterocyclic-carbene catalysts.  |  Azpíroz, R., et al. 2013. Chemistry. 19: 3812-6. PMID: 23436384
  6. A direct comparison of methods used to measure oxidized glutathione in biological samples: 2-vinylpyridine and N-ethylmaleimide.  |  Mcgill, MR. and Jaeschke, H. 2015. Toxicol Mech Methods. 25: 589-95. PMID: 26461121
  7. Enhanced Adsorption of Bisphenol A from Aqueous Solution with 2-Vinylpyridine Functionalized Magnetic Nanoparticles.  |  Li, Q., et al. 2018. Polymers (Basel). 10: PMID: 30961062
  8. Photophysical Properties and Kinetic Studies of 2-Vinylpyridine-Based Cycloplatinated(II) Complexes Containing Various Phosphine Ligands.  |  Dolatyari, V., et al. 2021. Molecules. 26: PMID: 33918450
  9. Visible-Light-Induced Photocatalytic Synthesis of β-Keto Dithiocarbamates via Difunctionalization of Styrenes.  |  Vishwakarma, RK., et al. 2021. Org Lett. 23: 4147-4151. PMID: 33988029
  10. Preparation of Butadienylpyridines by Iridium-NHC-Catalyzed Alkyne Hydroalkenylation and Quinolizine Rearrangement.  |  Azpíroz, R., et al. 2021. Chemistry. 27: 11868-11878. PMID: 33998070
  11. Synthesis, characterisation and functionalisation of BAB-type dual-responsive nanocarriers for targeted drug delivery: evolution of nanoparticles based on 2-vinylpyridine and diethyl vinylphosphonate.  |  Saurwein, A., et al. 2021. RSC Adv. 11: 1586-1594. PMID: 35424109
  12. Antiproliferative activity and DNA binding studies of cyclometalated complexes of platinum(II) containing 2-vinylpyridine.  |  Mojaddami, A., et al. 2022. Biometals. 35: 617-627. PMID: 35445906
  13. Heteronuclear, Monomer-Selective Zn/Y Catalyst Combines Copolymerization of Epoxides and CO2 with Group-Transfer Polymerization of Michael-Type Monomers.  |  Denk, A., et al. 2020. ACS Macro Lett. 9: 571-575. PMID: 35648488
  14. Composition-Property Relationships of pH-Responsive Poly[(2-vinylpyridine)-co-(butyl methacrylate)] Copolymers for Reverse Enteric Coatings.  |  Brewer, K. and Blencowe, A. 2023. Pharmaceutics. 15: PMID: 36839776

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Vinylpyridine, 25 ml

sc-254296
25 ml
$51.00

2-Vinylpyridine, 500 ml

sc-254296A
500 ml
$153.00