4,7-dibromotricyclo[5.2.1.0~2,6~]deca-4,8-diene-3,10-dione

Base Information

• Chemical Name: 4,7-dibromotricyclo[5.2.1.0~2,6~]deca-4,8-diene-3,10-dione
• CAS No.: 32846-64-3
• Molecular Formula: C₁₀H₆Br₂O₂
• Molecular Weight: 317.964
• Hs Code.: 2914790090
• Mol file: 32846-64-3.mol

Synonyms:4,7-dibromotricyclo[5.2.1.0~2,6~]deca-4,8-diene-3,10-dione

Chemical Property of 4,7-dibromotricyclo[5.2.1.0~2,6~]deca-4,8-diene-3,10-dione

Chemical Property:

• Vapor Pressure: 3.32E-07mmHg at 25°C
• Boiling Point: 418.3°C at 760 mmHg
• Flash Point: 165.2°C
• PSA: 34.14000
• Density: 2.263g/cm³
• LogP: 1.98270

Purity/Quality:

99% ^*data from raw suppliers

4,7-Dibromotricyclo[5.2.1.0^{2,6}]deca-4,8-diene-3,10-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4,7-Dibromotricyclo[5.2.1.0^{2,6}]deca-4,8-diene-3,10-dione is a building block used in the synthesis of cubanes.

Technology Process of 4,7-dibromotricyclo[5.2.1.0~2,6~]deca-4,8-diene-3,10-dione

There total 7 articles about 4,7-dibromotricyclo[5.2.1.0~2,6~]deca-4,8-diene-3,10-dione 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: 93.0%

(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal (485318-53-4) → (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione (32846-64-3,65656-68-0)

Guidance literature:

With sulfuric acid; at 20 - 25 ℃; for 25h;

DOI:10.1016/j.bmcl.2013.12.087

Reference yield:

1,4-dioxaspiro[4.4]nonane (176-32-9) → (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione (32846-64-3,65656-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: bromine / 1,4-dioxane / 60 h / 10 - 20 °C / Inert atmosphere

2: sodium hydroxide / methanol / 3 h / Reflux

3: sulfuric acid / 25 h / 20 - 25 °C

With sulfuric acid; bromine; sodium hydroxide; In 1,4-dioxane; methanol;

DOI:10.1016/j.bmcl.2013.12.087

Reference yield:

2,2,5-tribromocyclopentanone ethylene acetal (25834-49-5) → (3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione (32846-64-3,65656-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / methanol / 3 h / Reflux

2: sulfuric acid / 25 h / 20 - 25 °C

With sulfuric acid; sodium hydroxide; In methanol;

DOI:10.1016/j.bmcl.2013.12.087

upstream raw materials:

1,4-dioxaspiro[4.4]nonane

2,2,5-tribromocyclopentanone ethylene acetal

(3aα,4β,7α,7aα)-2,4-dibromo-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene-1,8-dione bisethylene ketal

cyclopentanone

Downstream raw materials:

cubane-1,4-dicarboxylic acid

cubane-1,4-dicarboxylic acid dimethyl ester

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