5-Vinyl-2-norbornene

Base Information

• Chemical Name: 5-Vinyl-2-norbornene
• CAS No.: 117110-18-6
• Deprecated CAS: 827315-16-2,1135584-97-2,1135584-97-2
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.194
• European Community (EC) Number: 221-259-8
• NSC Number: 61529
• DSSTox Substance ID: DTXSID6029250
• Nikkaji Number: J1.819H
• Wikipedia: Vinyl_norbornene
• ChEMBL ID: CHEMBL3186510
• Mol file: 117110-18-6.mol

Synonyms:5,2-VNB;5-vinyl-2-norbornene

Chemical Property of 5-Vinyl-2-norbornene

Chemical Property:

• Boiling Point: 141°Cat760mmHg
• Flash Point: 26.2°C
• Density: 1.006g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 120.093900383
• Heavy Atom Count: 9
• Complexity: 155

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C=CC1CC2CC1C=C2

Technology Process of 5-Vinyl-2-norbornene

There total 15 articles about 5-Vinyl-2-norbornene 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: 55.0%

2-(5-norbornen-exo-2-yl)ethyl p-toluenesulfonate → 5-vinyl-8,9,10-trinorborn-2-ene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1)

Guidance literature:

With pyridine; for 12h; Heating;

DOI:10.1246/bcsj.60.1954

Reference yield: 0.3%

exo-vinylnorbornene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1) + endo-vinylnorbornene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1) → 4-ethenylcyclohexene (100-40-3) + bicyclo[4.3.0]nona-3,7-diene (3048-65-5) + 5-vinyl-2-norbornene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1) + dicyclopentadiene (77-73-6,933-60-8,1755-01-7,13257-74-4,25850-35-5,57429-84-2,109428-68-4,25038-78-2) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2)

Guidance literature:

at 150 ℃; for 69.6333h; Product distribution / selectivity; Pyrolysis;

Reference yield:

5-vinyl-bicyclo[2.2.1]hept-2-ene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1) → 5-vinyl-8,9,10-trinorborn-2-ene (3048-64-4,23890-32-6,25093-48-5,117110-17-5,117110-18-6,142037-50-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaBH₄, BF₃*O(C₂H₅)2, 2.)aq. NaOH, 30 percent aq. H₂O₂ / 1.) THF, RT, 3 h, 2.) THF/H₂O, 40 deg C, 3 h

2: 42.1 percent / iodine, potassium iodide, NaHCO₃ / dioxane; H₂O / 1 h / Ambient temperature

3: 48.7 percent / pyridine / Ambient temperature

4: 55 percent / pyridine / 12 h / Heating

With pyridine; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; dihydrogen peroxide; iodine; sodium hydrogencarbonate; potassium iodide; In 1,4-dioxane; water;

DOI:10.1246/bcsj.60.1954

upstream raw materials:

exo-vinylnorbornene

endo-vinylnorbornene

methyl-triphenylphosphonium iodide

exo-2-formylbicyclo[2.2.1]hept-5-ene

Downstream raw materials:

exo-2,3-epoxy-5-vinylbicyclo[2.2.1]heptane

2-(5-norbornen-endo-2-yl)ethyl p-toluenesulfonate

5-vinyl-8,9,10-trinorborn-2-ene

cyclopenta-1,3-diene

Refernces

• 1、 -. "PROCESS FOR PRODUCING HIGH PURITY EXO-ALKENYLNORBORNENE". Page/Page column 13-14. . Retrieved 2009/07/02.
• 2、 Inoue, Yoshiharu. "Useful Synthetic Routes to Pure exo-5-Vinyl-2-norbornene and endo-5-Vinyl-2-norbornene". . p. 1954 - 1956. Retrieved 2007/10/02.