2-Vinylnaphthalene

Base Information

• Chemical Name: 2-Vinylnaphthalene
• CAS No.: 827-54-3
• Molecular Formula: C12H10
• Molecular Weight: 154.211
• Hs Code.: 2902909090
• European Community (EC) Number: 212-573-6
• NSC Number: 177870
• UNII: HZD8LI91N1
• DSSTox Substance ID: DTXSID70862435
• Nikkaji Number: J149.740E
• Wikidata: Q27122545
• Metabolomics Workbench ID: 57700
• Mol file: 827-54-3.mol

Synonyms:polyvinylnaphthalene

Chemical Property of 2-Vinylnaphthalene

Chemical Property:

• Appearance/Colour: Tan powder
• Melting Point: 64-68 °C(lit.)
• Boiling Point: 270.9 °C at 760 mmHg
• Flash Point: 115.5 °C
• PSA: 0.00000
• Density: 1.031 g/cm³
• LogP: 3.48280
• Water Solubility.: INSOLUBLE
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 154.078250319
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi:Irritant
• Statements: R20/22:; R36/38:
• Safety Statements: S26:; S36:

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Naphthalenes
• Canonical SMILES: C=CC1=CC2=CC=CC=C2C=C1

Technology Process of 2-Vinylnaphthalene

There total 182 articles about 2-Vinylnaphthalene 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: 83.0%

dimethylsulfone (67-71-0) + 2-Naphthalenemethanol (1592-38-7) → 2-naphthylethylene (827-54-3,28406-56-6) + hydrogen (1333-74-0)

Guidance literature:

With 1,10-Phenanthroline; potassium tert-butylate; iron(II) chloride; In toluene; at 120 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.0c01173

Reference yield: 76.0%

dimethylsulfone (67-71-0) + 2-Naphthalenemethanol (1592-38-7) → 2-isopropenylnaphthalene (3710-23-4) + 2-naphthylethylene (827-54-3,28406-56-6)

Guidance literature:

With C₂₄H₂₀ClN₂OPRu; potassium tert-butylate; In 1,4-dioxane; at 125 ℃; for 5h; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1002/anie.201407281

Reference yield: 73.0%

Methyltriphenylphosphonium bromide (1779-49-3) + β-naphthaldehyde (66-99-9) → 2-naphthylethylene (827-54-3,28406-56-6) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With potassium carbonate; for 20h; steel ball-milling;

DOI:10.1021/ja017908p

upstream raw materials:

2-ethylnaphthalene

naphthalen-2-ethanol

2,2'-(ethane-1,1-diyl)dinaphthalene

naphthalen-2-yl(trimethylsilyl)methanone

Downstream raw materials:

benz-1,4-phenanthrenequinone

(E)-2-(2-nitrovinyl)naphthalene

β-naphthaldehyde

naphthalene-2-carboxylate

Refernces

Polymer supported naphthalene-catalysed lithiation reactions

10.1016/S0040-4039(97)10774-2

The research focuses on polymer-supported naphthalene-catalysed lithiation reactions. The key chemicals involved include functionalized mono or dichlorinated materials (la-6a), lithium, and a catalytic amount of a naphthalene-supported polymer (P-152). The polymer P-152 is prepared by radical copolymerisation of 2-vinylnaphthalene, styrene, and divinylbenzene. In the presence of various electrophiles such as MeSiCl, BuOH, BuCHO, PhCHO, Et2CO, c(C3H5)2CO, P&CO, (CH2)4CO, (CH3)2CO, PhCOMe, PhCH=NPh, the reactions lead to the expected products (lc-6c) after hydrolysis. The catalyst can be quantitatively recovered and reused multiple times without losing its activity. This method offers an advantageous approach to lithiation processes, allowing for easy recovery of the catalyst and yielding similar results to traditional solution-based methods.

Rhenium-catalyzed insertion of terminal alkenes into a C(sp²)-H bond and successive transfer hydrogenation

10.1016/j.jorganchem.2010.09.064

The study presents a rhenium-catalyzed method for synthesizing 2-alkenylbenzylamines from aromatic aldimines and alkenes. The process involves the activation of an aromatic C(sp2)-H bond, followed by the insertion of an alkene into this bond, beta-hydride elimination, and finally the hydrogenation of the imino group of the aromatic aldimine. The research demonstrates that using the rhenium-hydride complex catalyst [HRe(CO)4]n leads to high yields of 2-alkenylbenzylamines, contrasting with other rhenium catalysts which may lead to different products like quinolines via an aza-Diels-Alder reaction. The study also explores the scope of the reaction with various aldimines and alkenes, providing insights into the reaction mechanism and the factors influencing the product selectivity and yield.