Bicyclo(2.2.2)oct-2-ene, 5,6-bis(methylene)-

Base Information

• Chemical Name: Bicyclo(2.2.2)oct-2-ene, 5,6-bis(methylene)-
• CAS No.: 36528-62-8
• Molecular Formula: C₁₀H₁₂
• Molecular Weight: 132.205
• DSSTox Substance ID: DTXSID90957832
• Nikkaji Number: J1.520.420F
• Mol file: 36528-62-8.mol

Synonyms:36528-62-8;Bicyclo(2.2.2)oct-2-ene, 5,6-bis(methylene)-;Bicyclo[2.2.2]oct-2-ene,5,6-bis(methylene)-;DTXSID90957832;5,6-DIMETHYLIDENEBICYCLO[2.2.2]OCT-2-ENE

Chemical Property of Bicyclo(2.2.2)oct-2-ene, 5,6-bis(methylene)-

Chemical Property:

• Vapor Pressure: 0.997mmHg at 25°C
• Boiling Point: 184.6°C at 760 mmHg
• Flash Point: 45.8°C
• PSA: 0.00000
• Density: 0.93g/cm³
• LogP: 2.69480
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 132.093900383
• Heavy Atom Count: 10
• Complexity: 196

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=C1C2CCC(C1=C)C=C2

Technology Process of Bicyclo(2.2.2)oct-2-ene, 5,6-bis(methylene)-

There total 6 articles about Bicyclo(2.2.2)oct-2-ene, 5,6-bis(methylene)- 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: 96.0%

5,6-bis(iodomethyl)bicyclo[2.2.2]-oct-2-ene (361451-37-8) → 5,6-dimethylenebicyclo<2.2.2>octa-2-ene (36528-62-8)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)00684-0

Reference yield:

5-Chloromethanesulfonyl-6-methylene-bicyclo[2.2.2]oct-2-ene → 5,6-dimethylenebicyclo<2.2.2>octa-2-ene (36528-62-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; Yield given;

DOI:10.1021/ja00166a073

Reference yield:

p-toluenesulfonate of endo-2,3-bis(hydroxymethyl)bicyclo<2.2.2>oct-5-ene (54290-45-8) → 5,6-dimethylenebicyclo<2.2.2>octa-2-ene (36528-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / NaI / acetone

2: 96 percent / t-BuOK / 2-methyl-propan-2-ol

With potassium tert-butylate; sodium iodide; In acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)00684-0

upstream raw materials:

methyl bromide

C₁₄H₂₆N₂

5,6-bis(iodomethyl)bicyclo[2.2.2]-oct-2-ene

p-toluenesulfonate of endo-2,3-bis(hydroxymethyl)bicyclo<2.2.2>oct-5-ene