1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Base Information

• Chemical Name: 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• CAS No.: 1231160-83-0
• Molecular Formula: C14H17Br2NO2S
• Molecular Weight: 423.168
• Hs Code.: 2934999090
• Mol file: 1231160-83-0.mol

Synonyms:1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione;1,3-Dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Chemical Property of 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Chemical Property:

• Melting Point: 115-117℃
• Boiling Point: 452.2±45.0 °C(Predicted)
• PKA: -3.36±0.20(Predicted)
• PSA: 65.62000
• Density: 1.618
• LogP: 5.02340
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3-Dibromo-5-(2-ethylhexyl)-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:

• Uses: suzuki reaction This monomer is used in the synthesis of low band gap polymers for numerous OPV devices including bulk heterojunction solar cells.Used as an electron acceptor material (n-type semiconductor) in Polymer Solar Cells.

Technology Process of 1,3-BibroMo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

There total 9 articles about 1,3-BibroMo-5-(2-ethylhexyl)-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: 90.0%

2-Ethylhexylamine (104-75-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1231160-83-0)

Guidance literature:

2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione; In toluene; at 130 ℃; for 20h; Inert atmosphere;

With pyridine; sulfurous dibromide; In toluene; at 0 - 130 ℃; for 23h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 86.0%

2-Ethylhexylamine (104-75-6) + 2,5-dibromothiophene-3,4-dicarboxylic acid anhydryde (1015423-45-6) → 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1231160-83-0)

Guidance literature:

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

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

DOI:10.1021/ja502985g

Reference yield: 79.0%

5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1231160-82-9) → 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1231160-83-0)

Guidance literature:

With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.dyepig.2016.10.007

upstream raw materials:

5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

2-Ethylhexylamine

thiophene-3,4-dicarboxylic acid

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

Downstream raw materials:

5-(3-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)-5-(2-ethylhexyl)-4,6-dioxo-5,6-dihydro-thieno[3,4-c]pyrrol-1-yl)thiophene-2-carbaldehyde

Refernces

• 1、 Yuan, Dafei,Medina Rivero, Samara,Mayorga Burrezo, Paula,Ren, Longbin,Sandoval-Salinas, María E.,Grabowski, S?awomir J.,Casanova, David,Zhu, Xiaozhang,Casado, Juan. "Thieno[3,4-c]pyrrole-4,6-dione Oligothiophenes Have Two Crossed Paths for Electron Delocalization". . p. 13523 - 13534. Retrieved 2018.
• 2、 Lang, Caili,Fan, Jingzhe,Gao, Yueyue,Liu, Ming,Zhang, Yong,Guo, Fengyun,Zhao, Liancheng. "Synthesis, characterization and photovoltaic properties of dithienobenzodithiophene-based conjugated polymers". . p. 50 - 57. Retrieved 2016/10/26.