Bicyclo[2.2.2]octane

Base Information

• Chemical Name: Bicyclo[2.2.2]octane
• CAS No.: 280-33-1
• Molecular Formula: C8H14
• Molecular Weight: 110.199
• Hs Code.: 2902199090
• DSSTox Substance ID: DTXSID40182278
• Nikkaji Number: J78.951H
• Wikidata: Q83052931
• Mol file: 280-33-1.mol

Synonyms:1,4-Endoethylenecyclohexane;Cyclohexane, 1,4-endo-(1,2-ethanediyl)-

Chemical Property of Bicyclo[2.2.2]octane

Chemical Property:

• Vapor Pressure: 7.63mmHg at 25°C
• Melting Point: 169.85°C
• Refractive Index: 1.4710 (estimate)
• Boiling Point: 140.5°C at 760 mmHg
• Flash Point: 19.4°C
• PSA: 0.00000
• Density: 0.896g/cm³
• LogP: 2.58660
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 110.109550447
• Heavy Atom Count: 8
• Complexity: 55

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CCC1CC2

Technology Process of Bicyclo[2.2.2]octane

There total 28 articles about Bicyclo[2.2.2]octane 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: 97.0%

norbornene (931-64-6) → bicyclo[2,2,2]octane (280-33-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In hexane; at 20 - 22 ℃;

DOI:10.1021/ja00199a039

Reference yield: 50.5%

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → bicyclo[2,2,2]octane (280-33-1)

Guidance literature:

With potassium hydroxide; hydrogen; nickel; In ethanol;

Reference yield: 12.0%

secocubane (3104-90-3) → bicyclo<2.2.2>octane (280-33-1) + bicyclo<3.2.1>octane (6221-55-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4020(01)87593-1

upstream raw materials:

norbornene

bicyclo[2.2.2]octan-2-one semicarbazone

bicyclo[2.2.2]octane-1,4-dibromide

trans-N,N'-bis(bicyclo<2.2.2>oct-1-yl)diazene

Downstream raw materials:

bicyclo[2.2.2]octan-2-ol

2-chloro-bicyclo[2.2.2]octane

bicyclo[2.2.2]octan-1-ol

bicyclo[2.2.2]octan-2-one

Refernces

1,2,3,4,5,6-hexasila-7,8-distannabicyclo[2.2.2]octanes: A novel approach toward bicyclo derivatives of group 14 elements

10.1021/om010801q

The study focuses on the synthesis and characterization of novel bicyclo[2.2.2]octane derivatives containing only tin (Sn) and silicon (Si) atoms in their ring skeletons, specifically 1,2,3,4,5,6-hexasila-7,8-distannabicyclo[2.2.2]octanes. The chemicals used in the study include 1,4-dihalogen-substituted decamethylcyclohexasilanes (Si6Me10X2: X = F, Cl) and diorganodichlorostannanes (R2SnCl2: R = Me, Ph). These compounds were reacted in the presence of magnesium to yield the target stannasilanes 5 and 6. The purpose of these chemicals was to create new compounds with potential applications in materials science and organometallic chemistry, and to investigate the influence of organostannyl groups on the properties of cyclic oligosilanes. The synthesized compounds were characterized using NMR, MS, and elemental analysis, with the solid-state structure of compound 6 determined by X-ray crystallography.

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