5,11-Dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene

Base Information

• Chemical Name: 5,11-Dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene
• CAS No.: 94275-22-6
• Molecular Formula: C₁₆H₁₄Br₂
• Molecular Weight: 366.095
• NSC Number: 90645
• DSSTox Substance ID: DTXSID00293551
• Mol file: 94275-22-6.mol

Synonyms:94275-22-6;5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene;NSC90645;DTXSID00293551;NSC-90645;2,10-dibromotricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaene

Chemical Property of 5,11-Dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene

Chemical Property:

• Vapor Pressure: 7.08E-06mmHg at 25°C
• Boiling Point: 388°C at 760 mmHg
• Flash Point: 220.4°C
• Density: 1.589g/cm³
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 365.94418
• Heavy Atom Count: 18
• Complexity: 250

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2=CC=CC=C2CC(C3=CC=CC=C31)Br)Br

Technology Process of 5,11-Dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene

There total 2 articles about 5,11-Dibromo-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene 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: 95.0%

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene (1460-59-9) → 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctadiene (94275-22-6)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; Heating;

DOI:10.1055/s-2002-32542

Reference yield:

α,α'-dibromo-o-xylene (91-13-4) → 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctadiene (94275-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / Li / tetrahydrofuran / 20 °C / sonication

2: 95 percent / NBS / CCl₄ / Heating

With N-Bromosuccinimide; lithium; In tetrahydrofuran; tetrachloromethane;

DOI:10.1055/s-2002-32542

Reference yield:

5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctadiene (94275-22-6) → 2-[(3-oxo-1,3-dihydro-2-benzofuran-1-yl)methyl]benzoic acid (2975-71-5)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid

2: ethanolic NaOH

3: chromium (VI)-oxide; acetic acid

With chromium(VI) oxide; sodium hydroxide; acetic acid;

DOI:10.1021/ja01148a076

upstream raw materials:

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene

α,α'-dibromo-o-xylene

Downstream raw materials:

sym-dibenzo-1,5-cyclooctadiene-3,7-diyne

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene

2-[(3-oxo-1,3-dihydro-2-benzofuran-1-yl)methyl]benzoic acid

(5Z,11Z)-5,11-diphenyldibenzo[a,e][8]annulene