4-Vinylpyridine

{{Chembox

| ImageFile = 4-vinylpyridine-svg.svg

| ImageSize = 130

| ImageAlt =

| PIN = 4-Ethenylpyridine

| OtherNames = 4-VP

| Section1 = {{Chembox Identifiers

| CASNo = 100-43-6

| PubChem = 7502

| ChemSpiderID = 7221

| EC_number = 202-852-0

| UNII = I56G67XM8D

| Beilstein = 104506

| StdInChI=1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2

| StdInChIKey = KFDVPJUYSDEJTH-UHFFFAOYSA-N

| SMILES = C=CC1=CC=NC=C1

}}

| Section2 = {{Chembox Properties

| C=7|H=7|N=1

| MolarMass =

| Appearance = colorless liquid

| Density = 0.988 g/cm³

| MeltingPt =

| MeltingPt_notes =

| BoilingPtC = 62-65

| BoilingPt_notes = 15 mmHg

| Solubility = }}

| Section3 = {{Chembox Hazards

| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|226|301|314|315|317|319|330|334|411}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|272|273|280|284|285|301+310|301+330+331|302+352|303+361+353|304+340|304+341|305+351+338|310|320|321|330|332+313|333+313|337+313|342+311|362|363|370+378|391|403+233|403+235|405|501}}

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

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.{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}

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.{{cite journal |last1=Suttapitugsakul |first1=Suttipong |last2=Xiao |first2=Haopeng |last3=Smeekens |first3=Johanna |last4=Wu |first4=Ronghu |date=2017 |title=Evaluation and optimization of reduction and alkylation methods to maximize peptide identification with MS-based proteomics |url=http://xlink.rsc.org/?DOI=C7MB00393E |journal=Molecular BioSystems |language=en |volume=13 |issue=12 |pages=2574–2582 |doi=10.1039/C7MB00393E |issn=1742-206X |pmc=5698164 |pmid=29019370}} 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.{{cite journal |last1=Sechi |first1=Salvatore |last2=Chait |first2=Brian T. |date=1998-12-01 |title=Modification of Cysteine Residues by Alkylation. A Tool in Peptide Mapping and Protein Identification |url=https://pubs.acs.org/doi/10.1021/ac9806005 |journal=Analytical Chemistry |language=en |volume=70 |issue=24 |pages=5150–5158 |doi=10.1021/ac9806005 |pmid=9868912 |issn=0003-2700|url-access=subscription }}