N-vinylimidazole

Base Information

• Chemical Name: N-vinylimidazole
• CAS No.: 1072-63-5
• Deprecated CAS: 2055215-53-5
• Molecular Formula: C5H6N2
• Molecular Weight: 94.116
• Hs Code.: 29339900
• European Community (EC) Number: 214-012-0,608-353-8
• NSC Number: 248607,231574
• UNII: ODY9ION63A
• DSSTox Substance ID: DTXSID0061458
• Nikkaji Number: J26.587J
• Wikipedia: 1-Vinylimidazole
• Wikidata: Q27285596
• NCI Thesaurus Code: C184914
• ChEMBL ID: CHEMBL3929571
• Mol file: 1072-63-5.mol

Synonyms:1-ethenyl-1H-imidazole;1-vinylimidazole;N-VI cpd;N-vinylimidazole

Chemical Property of N-vinylimidazole

Chemical Property:

• Appearance/Colour: Colorless to faint yellow transparent liquid
• Vapor Pressure: 0.506mmHg at 25°C
• Melting Point: 78-79 ºC
• Refractive Index: n20/D 1.533(lit.)
• Boiling Point: 191.8 ºC at 760 mmHg
• PKA: 6.07±0.10(Predicted)
• Flash Point: 69.8 ºC
• PSA: 17.82000
• Density: 1.038 g/cm³
• LogP: 0.98360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• Water Solubility.: Miscible with water.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 94.053098200
• Heavy Atom Count: 7
• Complexity: 70.5

Purity/Quality:

99% ^*data from raw suppliers

1-Vinylimidazole(StabilizedwithHydroquinone) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F
• Hazard Codes: C,F
• Statements: 22-34-41
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: C=CN1C=CN=C1
• General Description: Vinylimidazole, also known as 1-vinyl-1H-imidazole or N-vinylimidazole, is a key monomer used in the synthesis of polymerized functional ionic liquids, such as the homopolymer of 3-(cyanomethyl)-1-vinylimidazolium hexafluorophosphate, which serves as a support for palladium nanoparticles in catalytic applications. Vinylimidazole plays a crucial role in creating recyclable heterogeneous catalysts for reductive homocoupling reactions of aryl halides, enabling the efficient formation of biaryls under mild conditions. The resulting catalyst demonstrates good activity and selectivity, though minor deactivation occurs due to palladium leaching and nanoparticle aggregation. Vinylimidazole's versatility in polymer-supported catalytic systems highlights its importance in sustainable chemical synthesis.

Technology Process of N-vinylimidazole

There total 12 articles about N-vinylimidazole 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: 95.1%

→ 1-vinylimidazole (1072-63-5,25232-42-2)

Guidance literature:

Reference yield: 95.0%

2-(imidazol-1-yl)ethyl chloride (92952-84-6) → 1-vinylimidazole (1072-63-5,25232-42-2)

Guidance literature:

With potassium hydroxide; hydroquinone; In isopropyl alcohol; for 2h; Heating;

DOI:10.1080/00397910008086974

Reference yield: 71.0%

1H-imidazole (288-32-4) + vinyl acetate (108-05-4,9003-20-7) → 1-vinylimidazole (1072-63-5,25232-42-2)

Guidance literature:

With mercury(II) diacetate; hydroquinone; trifluoroacetic acid; at 70 ℃; for 3h;

DOI:10.1023/A:1020874201056

upstream raw materials:

1H-imidazole

acetylene

1,2-dichloro-ethane

ethylene dibromide

Downstream raw materials:

1-vinyl-2-hydroxymethylimidazole

C₁₁H₁₀ClN₂OP

1-(1-phenylethyl)-1H-imidazole

1-vinyl-3-butylimidazolium chloride

Refernces

Polymerized functional ionic liquid supported Pd nanoparticle catalyst for reductive homocoupling of aryl halides

10.1007/s00706-013-0925-7

This research presents the development of a heterogeneous palladium catalyst supported by a polymerized functional ionic liquid for the reductive homocoupling of aryl halides. The purpose of the study was to create a recyclable catalyst that could selectively catalyze the formation of biaryls, which are important building blocks in pharmaceuticals and agrochemicals, under mild conditions. The researchers synthesized a homopolymer of 3-(cyanomethyl)-1-vinylimidazolium hexafluorophosphate and used it to support Pd nanoparticles, resulting in the Pd@poly-CN-PF6 catalyst. This catalyst was found to efficiently catalyze the homocoupling reactions of aryl halides in water at 100°C with good yields. The catalyst could be recycled and reused multiple times with only a slight loss in activity, which was attributed to palladium leaching at high temperature and aggregation of palladium nanoparticles. Key chemicals used in the process included 1-vinylimidazole, 2-chloroacetonitrile, potassium hexafluorophosphate, azodiisobutyronitrile (AIBN), and sodium borohydride (NaBH4) for the synthesis of the polymer and the Pd nanoparticles, as well as aryl halides, NaOH, and ascorbic acid in the catalytic reactions.