4,7-Bis(5-bromo-2-thienyl)-2,1,3-benzoselenadiazole

Base Information

• Chemical Name: 4,7-Bis(5-bromo-2-thienyl)-2,1,3-benzoselenadiazole
• CAS No.: 534591-72-5
• Molecular Formula: C14H6Br2N2S2Se
• Molecular Weight: 505.11
• Mol file: 534591-72-5.mol

Synonyms:

Chemical Property of 4,7-Bis(5-bromo-2-thienyl)-2,1,3-benzoselenadiazole

Chemical Property:

• Boiling Point: 554.8±60.0 °C(Predicted)
• PKA: -1.49±0.50(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

4,7-Bis(5-bromothiophen-2-yl)benzo[c][1,2,5]selenadiazole 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,7-Bis(5-bromo-2-thienyl)-2,1,3-benzoselenadiazole

There total 7 articles about 4,7-Bis(5-bromo-2-thienyl)-2,1,3-benzoselenadiazole 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: 54.0%

4,7-di(thiophen-2-yl)benzo[c][1,2,5]-selenadiazole (711026-55-0) → 4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]selenadiazole (534591-72-5)

Guidance literature:

With N-Bromosuccinimide; acetic acid; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.202001210

Reference yield:

4,7-dibromobenzo[1,2,5]selenadiazole (63224-42-0) → 4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]selenadiazole (534591-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tributyltin chloride; lithium bromide

2: N-Bromosuccinimide

With N-Bromosuccinimide; tributyltin chloride; lithium bromide; 1: Stille coupling;

DOI:10.1016/j.polymer.2010.04.057

Reference yield:

1,2-diamino-benzene (95-54-5) → 4,7-bis(5-bromothiophen-2-yl)benzo[c][1,2,5]selenadiazole (534591-72-5)

Guidance literature:

Multi-step reaction with 4 steps

1: selenium(IV) oxide / 0.5 h / 75 °C

2: bromine; silver sulfate; sulfuric acid / 2 h / 20 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 20 h / Reflux

4: acetic acid; N-Bromosuccinimide / 20 °C / Inert atmosphere

With selenium(IV) oxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; bromine; silver sulfate; acetic acid; In toluene; 3: |Stille Cross Coupling;

DOI:10.1002/chem.202001210

upstream raw materials:

4,7-di(thiophen-2-yl)benzo[c][1,2,5]-selenadiazole

4,7-dibromobenzo[1,2,5]selenadiazole

benzo[1,2,5]thiadiazole

4,7-dibromobenzo[c][1,2,5]thiadiazole

Refernces

• 1、 Jung, I.N.Hwan,Hqyeon, Kim,Park, Moo-Jin,Kim, Bongjun,Park, Jong-Hwa,Jeong, Eunjae,Woo, Han Young,Yoo, Seunghyup,Shim, Hong-K.U.. "Synthesis and characterization of cyclopentadithiophene-based low bandgap copolymers containing electron-deficient benzoselenadiazole derivatives for photovoltaic devices". experimental part. p. 1423 - 1432. Retrieved 2011/03/19.