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:

1,2-bis(pyridin-2-yl)ethane

2-(3-phenylpropyl)pyridine

1,3-bis(2-pyridyl)propane

1,1'-(1,2-ethanediyl)bisbenzene

Refernces

• 1、 Wang, Peng,Liu, Hengzhi,Liu, Mengmeng,Li, Rong,Ma, Jiantai. "Immobilized Pd complexes over HMMS as catalysts for Heck cross-coupling and selective hydrogenation reactions". . p. 1138 - 1143. Retrieved 2014.
• 2、 Johnson, M. D.,Tobe, M. L.,Wong, L. Y.. "-". . . Retrieved 1968.
• 3、 Niwa, Takashi,Yorimitsu, Hideki,Oshima, Koichiro. "Palladium-catalyzed 2-pyridylmethyl transfer from 2-(2-pyridyl)-ethanol derivatives to organic halides by chelation-assisted cleavage of unstrained Csp3-Csp3 bonds". . p. 2643 - 2645. Retrieved 2007.
• 4、 Wakatsuki,Yamazaki. "-". . p. 26. Retrieved 1976.
• 5、 Sun, Maolin,Yang, Jingxin,Fu, Youtian,Liang, Chaoming,Li, Hong,Yan, Guoming,Yin, Chao,Yu, Wei,Ma, Yueyue,Cheng, Ruihua,Ye, Jinxing. "Continuous Flow Process for the Synthesis of Betahistine via Aza-Michael-Type Reaction in Water". . p. 1160 - 1166. Retrieved 2021.
• 6、 Boennemann, Helmut,Brijoux, Werner,Brinkmann, Rainer,Meurers, Willi. "Steuerung der katalytischen Pyridinsynthese aus Alkinen und Nitrilen durch (η6-Borinato)-Liganden am Cobalt". . p. 1616 - 1624. Retrieved 1984.
• 7、 Lightfoot, Andrew P.,Twiddle, Steven J. R.,Whiting, Andrew. "4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane: An efficient and selective 2-carbon building block for vinylboronate Suzuki-Miyaura coupling reactions". . p. 529 - 531. Retrieved 2005.
• 8、 Lee, Dong-Hwan,Jung, Ji-Young,Jin, Myung-Jong. "Highly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides". . p. 2024 - 2029. Retrieved 2010.
• 9、 Shigeno, Masanori,Shishido, Yoshiteru,Hayashi, Kazutoshi,Nozawa-Kumada, Kanako,Kondo, Yoshinori. "KO-t-Bu Catalyzed Thiolation of β-(Hetero)arylethyl Ethers via MeOH Elimination/hydrothiolation". supporting information. p. 3932 - 3935. Retrieved 2021/08/24.