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
• General Description: 4-Vinylpyridine is a versatile building block in organic synthesis, particularly in photocatalyzed reactions for producing alkylpyridines. It reacts with various hydrogen donors under mild, eco-friendly conditions (e.g., sunlight or flow systems) using decatungstate photocatalysis, enabling efficient and sustainable access to biologically relevant pyridine derivatives, such as pharmaceutical intermediates or flavor compounds. The process highlights its utility in green chemistry due to its operational simplicity and reduced environmental impact.

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

Vinylpyridines as Building Blocks for the Photocatalyzed Synthesis of Alkylpyridines

10.1002/chem.201701346

The study focuses on the photocatalyzed synthesis of alkylpyridines using vinylpyridines as building blocks. The researchers utilized a decatungstate salt as a photocatalyst to facilitate the addition of various hydrogen donors, such as ethers, aldehydes, alkanes, and amides, onto vinylpyridines under sunlight or flow conditions. This approach successfully yielded alkylpyridines, which are significant as they serve as building blocks for compounds with biological activity, including those with potential pharmaceutical uses and umami flavor. The process is straightforward, cost-effective, and environmentally friendly, as it minimizes the use of harmful reagents and can be conducted using natural sunlight, showcasing the potential for green and sustainable chemical synthesis.