2-Vinylpyridine

Base Information

• Chemical Name: 2-Vinylpyridine
• CAS No.: 100-69-6
• Molecular Formula: C7H7N
• Molecular Weight: 105.139
• Hs Code.: 29333999
• European Community (EC) Number: 202-879-8,626-300-7
• ICSC Number: 1232
• NSC Number: 118993,18255
• UN Number: 3073
• UNII: DT4UV4NNKX
• DSSTox Substance ID: DTXSID1026667
• Nikkaji Number: J38.336H
• Wikipedia: 2-Vinylpyridine
• Wikidata: Q4596922
• ChEMBL ID: CHEMBL2134875
• Mol file: 100-69-6.mol

Synonyms:2-vinylpyridine

Chemical Property of 2-Vinylpyridine

Chemical Property:

• Appearance/Colour: dark brown liquid with an unpleasant odour
• Vapor Pressure: 10 mm Hg ( 44.5 °C)
• Melting Point: -50 °C
• Refractive Index: n20/D 1.549(lit.)
• Boiling Point: 160.3 °C at 760 mmHg
• PKA: pK1:4.98(+1) (25°C)
• Flash Point: 46.7 °C
• PSA: 12.89000
• Density: 0.968 g/cm³
• LogP: 1.72460
• Storage Temp.: 2-8°C
• Solubility.: 27g/l
• Water Solubility.: 2.5 g/100 mL (20 ºC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 105.057849228
• Heavy Atom Count: 8
• Complexity: 78.5
• Transport DOT Label: Poison Flammable Liquid Corrosive

Purity/Quality:

99.9% ^*data from raw suppliers

2-Vinylpyridine(stabilizedwith0.1%4-tert-butylcatechol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,C,F
• Hazard Codes: T,C,F,N
• Statements: 10-20-25-34-42/43-36-51/53-43-21/22
• Safety Statements: 16-23-26-36/37/39-45-28A-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C=CC1=CC=CC=N1
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the skin. This may result in delayed burns. The substance is severely irritating to the eyes and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: 2-Vinylpyridine is a pyridine deriviative used in the preparation of poly(2-vinylpyridine) via radical polymerization. 2-Vinylpyridine is used to improve effectiveness of protective polymer coatings o n metals. 2-Vinylpyridine is an impurity of Betahistine (B324000). 2-Vinylpyridine is a pyridine derivative used in the preparation of poly(2-vinylpyridine) via radical polymerization. 2-Vinylpyridine is used to improve effectiveness of protective polymer coatings on metals. It is a reagent for pyridylethylation for new protection method for active hydrogen compounds.. It is also used as basic materials for one of largest-selling plastic, manufacturing pharmaceuticals and bio-compounds.

Technology Process of 2-Vinylpyridine

There total 63 articles about 2-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: 99.0%

2-ethynylpyridine (1945-84-2) → 2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6)

Guidance literature:

With hydrogen; In toluene; at 20 ℃; for 12h; under 22801.5 Torr; chemoselective reaction; Autoclave;

DOI:10.1021/jacs.5b07521

Reference yield: 92.3%

diethyl-(2-pyridin-2-yl-ethyl)-amine (25877-30-9) → 2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6)

Guidance literature:

Reference yield: 86.0%

pyridine-2-carbaldehyde (1121-60-4) + diazomethyl-trimethyl-silane (18107-18-1) → 2-vinylpyridine (100-69-6,25014-15-7,27476-03-5,329041-71-6)

Guidance literature:

With (IMes)CuCl; triphenylphosphine; isopropyl alcohol; In 1,4-dioxane; diethyl ether; at 60 ℃; for 16h;

DOI:10.1021/jo061781a

upstream raw materials:

α-picoline

formaldehyd

2-Ethylpyridine

2-(2-Hydroxyethyl)pyridine

Downstream raw materials:

2-[2-(pyrrolidin-1-yl)ethyl]pyridine

2-[2-(piperidyl)ethyl]pyridine

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

1,3-bis(2-pyridyl)propane

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.

Cycloplatinated(II) complex bearing 2-vinylpyridine and monodentate phosphine ligands: Optical properties and kinetic study

10.1016/j.jorganchem.2015.12.005

The study focuses on the synthesis, characterization, and kinetic investigation of a cycloplatinated(II) complex bearing 2-vinylpyridine and monodentate phosphine ligands. The main chemical used was the 2-vinylpyridinate complex [PtMe(Vpy)(DMSO)], denoted as complex C, which was prepared from the dimeric platinum(II) complex cis,cis-[Me2Pt(m-SMe2)2PtMe2], known as complex B, in the presence of DMSO (dimethyl sulfoxide) and 2-vinylpyridine ligand. The DMSO molecule in complex C was substituted by methyldiphenylphosphine (PPh2Me) to synthesize [PtMe(Vpy)(PPh2Me)], referred to as complex 1. This complex was characterized by its optical properties, showing intense phosphorescence emission in solid state and solution, and was attributed to a mixed 3ILCT/3MLCT excited state. The study also investigated the oxidative addition reaction of complex 1 with alkyl halide (MeI), resulting in the formation of [PtMe2I(Vpy)(PPh2Me)], known as complex 2. Kinetic studies suggested that this reaction proceeded via a classical SN2 mechanism, and the rate of the reaction at different temperatures was measured, yielding a high negative DS# value that supported the proposed mechanism. The study serves to understand the reactivity of cycloplatinated complexes and their potential applications in fields such as optoelectronics and medicinal chemistry.

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