4-Vinylpyridine

Base Information

• Chemical Name: 4-Vinylpyridine
• CAS No.: 100-43-6
• Deprecated CAS: 80347-34-8
• Molecular Formula: C7H7N
• Molecular Weight: 105.139
• Hs Code.: 29333990
• European Community (EC) Number: 202-852-0,684-212-4
• NSC Number: 18256
• UNII: I56G67XM8D
• DSSTox Substance ID: DTXSID0051499
• Nikkaji Number: J38.337F
• Wikipedia: 4-Vinylpyridine
• Wikidata: Q13427555
• ChEMBL ID: CHEMBL4550330
• Mol file: 100-43-6.mol

Synonyms:4-ethenylpyridine;4-vinylpyridine;4-vinylpyridine hydrobromide;4-vinylpyridine hydrochloride;4-vinylpyridine ion (1-);4-vinylpyridine nitrate;4-vinylpyridine perchlorate;4-vinylpyridine sulfate (1:1);HI of 4-vinylpyridine

Chemical Property of 4-Vinylpyridine

Chemical Property:

• Appearance/Colour: dark brown to yellow liquid
• Vapor Pressure: 1.68mmHg at 25°C
• Melting Point: < 25oC
• Refractive Index: n20/D 1.549(lit.)
• Boiling Point: 173.627 °C at 760 mmHg
• PKA: pK1:5.62(+1) (25°C)
• Flash Point: 51.667 °C
• PSA: 12.89000
• Density: 0.968 g/cm³
• LogP: 1.72460
• Storage Temp.: -20°C
• Water Solubility.: 29 G/L (20 ºC)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 105.057849228
• Heavy Atom Count: 8
• Complexity: 72.5

Purity/Quality:

99% ^*data from raw suppliers

4-Vinylpyridine(stabilizedwithhydroquinone) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-25-34-42/43-23/25
• Safety Statements: 23-26-36/37/39-45-28A-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C=CC1=CC=NC=C1
• Uses: 4-Vinylpyridine acts as a co-monomer in styrene-butadiene polymers to promote adhesion between the rubber compound and supporting fibers (or cords) in tires, belts and hoses. It serves as an intermediate for manufacturing chemicals and pharmaceuticals. Further, it is used as a reagent for the modification of cysteine. In addition to this, it is used to make poly(4-vinylpyridine) and elastomers.

Technology Process of 4-Vinylpyridine

There total 38 articles about 4-Vinylpyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

4-(2-hydroxyethyl)pyridine (5344-27-4) + methyl 2-[2-(3,5-dimethylphenyl)-3-((1S)-1-methyl-2-{[(2,4-nitrophenyl)sulfonyl]amino}ethyl)-1H-indol-5-yl]-2-methylpropanoate (648894-30-8) → 4-vinylpyridine (100-43-6,329041-72-7) + methyl 2-(2-(3,5-dimethylphenyl)-3-{(1S)-2-[[(,4-dinitrophenyl)sulfonyl](2-pyridin-4-ylethyl)amino]-1-methylethyl}-1H-indol-5-yl)-2-methylpropanoate

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 10 ℃;

DOI:10.1016/j.tetasy.2003.08.038

Reference yield: 84.0%

4-bromopyridine hydrochloride (19524-06-2) + potassium vinyltrifluoroborate → 4-vinylpyridine (100-43-6,329041-72-7)

Guidance literature:

With C₁₇H₃₆ClN₆NiP₂⁽¹⁺⁾*Cl^(1-); potassium tert-butylate; In toluene; at 120 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01398

Reference yield: 76.0%

4-pyridineboronic acid pinacol ester (181219-01-2) → 4-vinylpyridine (100-43-6,329041-72-7)

Guidance literature:

4-pyridineboronic acid pinacol ester; vinylmagnesium halide; In tetrahydrofuran; at -78 - 20 ℃; for 2.25h; Inert atmosphere;

With trifluoroacetyl chloride; In tetrahydrofuran; at -78 - -40 ℃; for 18.5h; Further stages; Inert atmosphere;

DOI:10.1002/anie.201510027

upstream raw materials:

picoline

formaldehyd

4-(2-hydroxyethyl)pyridine

ethanol

Downstream raw materials:

4-(2-pyrrolidin-1-yl-ethyl)-pyridine

4-(2-(piperidin-1-yl)ethyl)pyridine

N-[2-(4-pyridyl)ethyl]morpholine

1-(morpholin-4-yl)-2-(pyridin-4-yl)ethanethione

Refernces

• 1、 Alunni, Sergio,Ottavi, Laura. "Mechanisms of Acid-Base Catalysis of β-Elimination Reactions in Systems Activated by a Pyridine Ring". . p. 2272 - 2283. Retrieved 2004.
• 2、 Mastalir, Matthias,St?ger, Berthold,Pittenauer, Ernst,Allmaier, Günter,Kirchner, Karl. "Air-Stable Triazine-Based Ni(II) PNP Pincer Complexes As Catalysts for the Suzuki-Miyaura Cross-Coupling". . p. 3186 - 3189. Retrieved 2016.
• 3、 Jeong, Jinu,Suzuki, Kosuke,Yamaguchi, Kazuya,Mizuno, Noritaka. "Visible-light-responsive catalysis of a zinc-introduced lacunary disilicoicosatungstate for the deoxygenation of pyridine N-oxides". . p. 13226 - 13229. Retrieved 2017.
• 4、 Frank et al.. "-". . p. 879,880. Retrieved 1948.
• 5、 Zhang, Yu-Lan,Wang, Gang-Hu,Wu, Yichen,Zhu, Chun-Yin,Wang, Peng. "Construction of α-Amino Azines via Thianthrenation-Enabled Photocatalyzed Hydroarylation of Azine-Substituted Enamides with Arenes". supporting information. p. 8522 - 8526. Retrieved 2021/11/13.
• 6、 -. "Oxidative Dehydroxymethylation of Alcohols to Produce Olefins". Paragraph 0057; 0058. . Retrieved 2019/09/06.