1,3-Dibromo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Base Information

• Chemical Name: 1,3-Dibromo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• CAS No.: 566939-58-0
• Molecular Formula: C14H17Br2NO2S
• Molecular Weight: 423.168
• Hs Code.: 2934999090
• Mol file: 566939-58-0.mol

Synonyms:K0260

Chemical Property of 1,3-Dibromo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Chemical Property:

• Vapor Pressure: 0.0±1.1 mmHg at 25°C
• Melting Point: 105.0 to 109.0 °C
• Boiling Point: 457.8±45.0 °C at 760 mmHg
• PKA: -3.32±0.20(Predicted)
• Flash Point: 230.7±28.7 °C
• PSA: 65.62000
• Density: 1.621
• LogP: 5.16750
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

97% ^*data from raw suppliers

1,3-Dibromo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Description: 1,3-Dibromo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione, also referred to as TPD-C8, is electron-deficient and used as a monomer for the synthesis of low band-gap polymer semiconductors in OPV and OFET applications.
• Uses: Used as an electron acceptor material (n-type semiconductor) in Polymer Solar Cells. suzuki reaction

Technology Process of 1,3-Dibromo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

There total 14 articles about 1,3-Dibromo-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-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: 84.0%

1-bromo-octane (111-83-1) + 1,3-dibromo-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1362606-94-7) → 1,3-dibromo-5-octylthieno[3,4-c]pyrrole-4,6-dione (566939-58-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.orglett.6b03830

Reference yield: 84.0%

n-Octylamine (111-86-4) + 2,5-dibromothiophene-3,4-dicarboxylic acid anhydryde (1015423-45-6) → 1,3-dibromo-5-octylthieno[3,4-c]pyrrole-4,6-dione (566939-58-0)

Guidance literature:

n-Octylamine; 2,5-dibromothiophene-3,4-dicarboxylic acid anhydryde; In tetrahydrofuran; at 50 ℃; for 3h; Inert atmosphere;

With thionyl chloride; In tetrahydrofuran; at 55 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ja400365b

Reference yield: 82.0%

5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (773881-43-9) → 1,3-dibromo-5-octylthieno[3,4-c]pyrrole-4,6-dione (566939-58-0)

Guidance literature:

With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20 ℃;

DOI:10.1002/asia.201301357

upstream raw materials:

5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

4-octylcarbamoylthiophene-3-carboxylic acid

1H,3H-thieno[3,4-c]furan-1,3-dione

thiophene-3,4-dicarboxylic acid