Bicyclo[2.2.2]oct-2-ene

Base Information

• Chemical Name: Bicyclo[2.2.2]oct-2-ene
• CAS No.: 931-64-6
• Molecular Formula: C8H12
• Molecular Weight: 108.183
• Hs Code.: 2902199090
• DSSTox Substance ID: DTXSID40239271
• Nikkaji Number: J110.355E
• Wikidata: Q83121604
• Mol file: 931-64-6.mol

Synonyms:bicyclo(2.2.2)oct-2-ene

Chemical Property of Bicyclo[2.2.2]oct-2-ene

Chemical Property:

• Vapor Pressure: 8.41mmHg at 25°C
• Melting Point: 111.4°C
• Refractive Index: 1.506
• Boiling Point: 138.3 °C at 760 mmHg
• Flash Point: 18.5 °C
• PSA: 0.00000
• Density: 0.93 g/cm³
• LogP: 2.36260
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 108.093900383
• Heavy Atom Count: 8
• Complexity: 91.2

Purity/Quality:

98%Min ^*data from raw suppliers

2,2,2-BICYCLO-2-OCTENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CCC1C=C2

Technology Process of Bicyclo[2.2.2]oct-2-ene

There total 35 articles about Bicyclo[2.2.2]oct-2-ene 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%

Bicyclo[2.2.2]octanon-(2)-p-toluolsulfonylhydrazonn (94064-42-3) → norbornene (931-64-6)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; methyllithium;

DOI:10.1021/ja0636035

Reference yield: 83.0%

endo-bicyclo<2.2.2>oct-5-en-2-ol mesylate → norbornene (931-64-6)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 60 ℃; for 4h;

DOI:10.1016/S0022-328X(98)01175-9

Reference yield: 78.5%

5-(phenylsulfonyl)bicyclo<2.2.2>oct-2-ene (77550-13-1) → norbornene (931-64-6)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In tetrahydrofuran; methanol; for 3.5h;

DOI:10.1021/jo00173a039

upstream raw materials:

Bicyclo<2.2.2>octane-2,3-di-exo-carboxylic anhydride

acetic acid bicyclo[2.2.2]oct-2-yl ester

bicyclo[2.2.2]oct-5-en-2-one

ethene

Downstream raw materials:

2,3-epoxybicyclo<2.2.2>oct-2-ene

2-exo-Benzolsulfonsaeureamido-8-syn-brom-bicyclo<3,2,1>octan

tricyclo<3.2.2.0^2,4>nonane

trans-3-aminobicyclo<2,2,2>octan-2-ol

Refernces

• 1、 Radlick et al.. "". . p. 5117. Retrieved 1968.
• 2、 Jung, Michael E.,Roberts, Courtney A.,Perez, Felix,Pham, Hung V.,Zou, Lufeng,Houk. "Thermodynamic Control of Isomerizations of Bicyclic Radicals: Interplay of Ring Strain and Radical Stabilization". supporting information. p. 32 - 35. Retrieved 2016/01/12.
• 3、 Powers, David C.,Leber, Phyllis A.,Gallagher, Sarah S.,Higgs, Andrew T.,McCullough, Lynne A.,Baldwin, John E.. "Thermal chemistry of bicyclo[4.2.0]oct-2-enes". . p. 187 - 194. Retrieved 2007/10/03.