5,6-Dibromocyclooctene

Base Information

• Chemical Name: 5,6-Dibromocyclooctene
• CAS No.: 24165-06-8
• Molecular Formula: C₈H₁₂Br₂
• Molecular Weight: 267.991
• NSC Number: 167076
• DSSTox Substance ID: DTXSID301314437
• Mol file: 24165-06-8.mol

Synonyms:24165-06-8;NSC167076;5,6-dibromocyclooctene;5,6-dibromo-1-cyclooctene;DTXSID301314437;NSC-167076

Chemical Property of 5,6-Dibromocyclooctene

Chemical Property:

• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: 1.547
• Boiling Point: 261.2 °C at 760 mmHg
• Flash Point: 124.6 °C
• Density: 1.634 g/cm³
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 267.92853
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(CCC=C1)Br)Br
• Isomeric SMILES: C/1CC(C(CC/C=C1)Br)Br

Technology Process of 5,6-Dibromocyclooctene

There total 5 articles about 5,6-Dibromocyclooctene 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: 90.0%

cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → (Z)-5,6-dibromocyclooct-1-ene (24165-06-8)

Guidance literature:

With bromine; In dichloromethane; at 20 ℃; for 0.833333h; under 760.051 Torr;

DOI:10.1021/acs.orglett.9b01863

Reference yield: 66.0%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → trans-5,6-Dibrom-(Z)-cycloocten (24165-06-8,67840-10-2,117468-09-4) + trans-1-bromo-2-fluorocyclooct-5-ene (106730-15-8)

Guidance literature:

With N-Bromosuccinimide; tetrabutylammonium hydrogen bifluoride; In dichloromethane; for 23h; Ambient temperature;

DOI:10.1021/jo00279a013

Reference yield: 43.0%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → (Z)-5,6-dibromocyclooct-1-ene (24165-06-8)

Guidance literature:

With bromine; In hexane; tert-butyl alcohol; at -5 - 20 ℃;

upstream raw materials:

1,5-cis,cis-cyclooctadiene

cyclo-octa-1,5-diene

Downstream raw materials:

(Z)-cyclooct-1-ene-5-yne

1-bromo-1,5-cyclooctadiene

C₂₁H₂₀BrNO

C₂₁H₂₁NO

Refernces

• 1、 Gunawardene, Praveen N.,Luo, Wilson,Polgar, Alexander M.,Corrigan, John F.,Workentin, Mark S.. "Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition". supporting information. p. 5547 - 5551. Retrieved 2019/08/01.
• 2、 Camps, F.,Chamorro, E.,Gasol, V.,Guerrero, A.. "Efficient Utilization of Tetrabutylammonium Bifluoride in Halofluorination Reactions". . p. 4294 - 4298. Retrieved 2007/10/02.