4,7-dibroMo-5-fluorobenzo[c][1,2,5]thiadiazole

Base Information

• Chemical Name: 4,7-dibroMo-5-fluorobenzo[c][1,2,5]thiadiazole
• CAS No.: 1347736-74-6
• Molecular Formula: C6HBr2FN2S
• Molecular Weight: 311.96
• Mol file: 1347736-74-6.mol

Synonyms:4,7-dibroMo-5-fluorobenzo[c][1,2,5]thiadiazole;2,1,3-Benzothiadiazole, 4,7-dibroMo-5-fluoro-;4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole;Dibromo-FBT;5-fluoro-4,7-dibromo-[2,1,3]benzothiadiazole;4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole >=99% (HPLC)

Chemical Property of 4,7-dibroMo-5-fluorobenzo[c][1,2,5]thiadiazole

Chemical Property:

• Melting Point: 160.0 to 164.0 °C
• Boiling Point: 321.3±37.0 °C(Predicted)
• PKA: -4.32±0.50(Predicted)
• PSA: 54.02000
• Density: 2.292±0.06 g/cm3(Predicted)
• LogP: 3.35540
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: soluble in Toluene

Purity/Quality:

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

4,7-Dibromo-5-fluoro-2,1,3-benzothiadiazole ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Monomer for synthesis of polymers for high power conversion efficiency (PCE) organic solar cells and high mobility OFETs.Fluorination lowers the polymer HOMO level; resulting in high open-circuit voltages well exceeding 0.7 V.High-Efficiency Polymer F-PCPDTBT:PC70BM Bulk Heterojuction Organic Solar Cells (OPVs):JSC = 14.1 mA/cm2VOC = 0.74 VFF = 0.58PCE = 6.2%

Technology Process of 4,7-dibroMo-5-fluorobenzo[c][1,2,5]thiadiazole

There total 11 articles about 4,7-dibroMo-5-fluorobenzo[c][1,2,5]thiadiazole 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: 88.0%

3,6-dibromo-4-fluoro-1,2-phenylenediamine (1347736-83-7) → 4,7-dibromo-5-fluoro-benzo[c][1,2,5]thiadiazole (1347736-74-6)

Guidance literature:

With pyridine; thionyl chloride; at 0 - 20 ℃; for 72h;

DOI:10.1039/c1cc14586j

Reference yield: 57.0%

5-fluorobenzo[c][1,2,5]thiadiazole (17821-75-9) → 4,7-dibromo-5-fluoro-benzo[c][1,2,5]thiadiazole (1347736-74-6)

Guidance literature:

With hydrogen bromide; bromine; In water; for 48h; Reflux;

Reference yield:

4-fluoro-1,2-phenylenediamine (367-31-7) → 4,7-dibromo-5-fluoro-benzo[c][1,2,5]thiadiazole (1347736-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride; triethylamine / chloroform / 4 h / Reflux

2: hydrogen bromide; bromine / 48 h / 128 °C

With thionyl chloride; hydrogen bromide; bromine; triethylamine; In chloroform;

DOI:10.1002/adma.201201127

upstream raw materials:

2,5-dibromo-4-fluoroaniline

N-(2,5-dibromo-4-fluorophenyl)-2,2,2-trifluoroacetamide

N-(2,5-dibromo-4-fluoro-6-nitrophenyl)-2,2,2-trifluoroacetamide

2,5-dibromo-4-fluoro-6-nitroaniline

Downstream raw materials:

4-bromo-5-fluoro-7-(5'-hexyl-[2,2'-bi-thiophene]-5-yl)benzo[c][1,2,5]thiadiazole

5,8-dibromo-6-fluoro-2,3-diphenylquinoxaline

5,8-dibromo-6-fluoro-2,3-bis(3-(octyloxy)phenyl)quinoxaline

5-fluoro-4,7-bis(5-trimethylstannyl-thien-2-yl)benzo-2,1,3-thiadiazole

Refernces

• 1、 Wang, Lihui,Yin, Lunxiang,Ji, Changyan,Li, Yanqin. "Tuning the photovoltaic performance of BT-TPA chromophore based solution-processed solar cells through molecular design incorporating of bithiophene unit and fluorine-substitution". . p. 37 - 44. Retrieved 2015.
• 2、 Albrecht, Steve,Janietz, Silvia,Schindler, Wolfram,Frisch, Johannes,Kurpiers, Jona,Kniepert, Juliane,Inal, Sahika,Pingel, Patrick,Fostiropoulos, Konstantinos,Koch, Norbert,Neher, Dieter. "Fluorinated copolymer PCPDTBT with enhanced open-circuit voltage and reduced recombination for highly efficient polymer solar cells". . p. 14932 - 14944. Retrieved 2012.
• 3、 Chao, Pengjie,He, Feng,Lai, Hanjian,Lin, Li,Mo, Daize,Tian, Leilei,Zhang, Qingwen. "Chlorination: Vs. fluorination: A study of halogenated benzo [c] [1,2,5]thiadiazole-based organic semiconducting dots for near-infrared cellular imaging". . p. 7740 - 7748. Retrieved 2020/06/10.
• 4、 -. "INERT SOLUTION-PROCESSABLE MOLECULAR CHROMOPHORES FOR ORGANIC ELECTRONIC DEVICES". . . Retrieved 2019/11/12.