Propanedinitrile, 2-[[7-[5-[bis(4-Methylphenyl)aMino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]Methylene]-

Base Information

• Chemical Name: Propanedinitrile, 2-[[7-[5-[bis(4-Methylphenyl)aMino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]Methylene]-
• CAS No.: 1335150-09-8
• Molecular Formula: C28H19N5S2
• Molecular Weight: 489.624
• Hs Code.: 2934999090
• Mol file: 1335150-09-8.mol

Synonyms:Propanedinitrile, 2-[[7-[5-[bis(4-Methylphenyl)aMino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]Methylene]-;2-[[7-[5-[Bis(4-methylphenyl)amino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]methylene]propanedinitrile;2-{[7-(5-N,N-Ditolylaminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile

Chemical Property of Propanedinitrile, 2-[[7-[5-[bis(4-Methylphenyl)aMino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]Methylene]-

Chemical Property:

• Melting Point: 230-235°C
• Boiling Point: 712.4±60.0 °C(Predicted)
• PKA: -0.55±0.50(Predicted)
• PSA: 133.08000
• Density: 1.352±0.06 g/cm3(Predicted)
• LogP: 7.93696

Purity/Quality:

99% ^*data from raw suppliers

2-{[7-(5-N,N-Ditolylaminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile 99% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

Useful:

• Uses: DTDCTB is a π-conjugating polymer that can be used in the fabrication of organic solar cells (OSCs) and organic photovoltaic cells (OPVs).

Technology Process of Propanedinitrile, 2-[[7-[5-[bis(4-Methylphenyl)aMino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]Methylene]-

There total 4 articles about Propanedinitrile, 2-[[7-[5-[bis(4-Methylphenyl)aMino]-2-thienyl]-2,1,3-benzothiadiazol-4-yl]Methylene]- 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: 55.0%

5-(N,N-di-p-tolylamino)-2-(tri-n-butylstannyl)thiophene (1256269-42-7) + 2-((7-bromobenzo[c][1,2,5]thiadiazol-4-yl)methylene)malononitrile (1335150-10-1) → 2-{[7-(5-(N,N-di-p-tolyl)aminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile (1335150-09-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 110 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ja205126t

Reference yield:

4-bromo-7-dibromomethyl-2,1,3-benzothiadiazole (1239277-96-3) → 2-{[7-(5-(N,N-di-p-tolyl)aminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile (1335150-09-8)

Guidance literature:

Multi-step reaction with 3 steps

1: silver nitrate / water; acetonitrile / 2 h / Reflux; Inert atmosphere

2: aluminum oxide / toluene / 2 h / 70 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 110 °C / Inert atmosphere

With aluminum oxide; bis-triphenylphosphine-palladium(II) chloride; silver nitrate; In water; toluene; acetonitrile; 2: Knoevenagel condensation / 3: Stille coupling;

DOI:10.1021/ja205126t

Reference yield:

4-bromo-7-methylbenzo[c][1,2,5]thiadiazole (2255-80-3) → 2-{[7-(5-(N,N-di-p-tolyl)aminothiophen-2-yl)-2,1,3-benzothiadiazol-4-yl]methylene}malononitrile (1335150-09-8)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 4 h / 80 °C / Inert atmosphere

2: silver nitrate / water; acetonitrile / 2 h / Reflux; Inert atmosphere

3: aluminum oxide / toluene / 2 h / 70 °C / Inert atmosphere

4: bis-triphenylphosphine-palladium(II) chloride / toluene / 2 h / 110 °C / Inert atmosphere

With aluminum oxide; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); silver nitrate; In water; chlorobenzene; toluene; acetonitrile; 3: Knoevenagel condensation / 4: Stille coupling;

DOI:10.1021/ja205126t

upstream raw materials:

4-bromo-7-dibromomethyl-2,1,3-benzothiadiazole

5-(N,N-di-p-tolylamino)-2-(tri-n-butylstannyl)thiophene

2-((7-bromobenzo[c][1,2,5]thiadiazol-4-yl)methylene)malononitrile

4-bromo-7-methylbenzo[c][1,2,5]thiadiazole

Refernces

• 1、 Chen, Yi-Hong,Lin, Li-Yen,Lu, Chih-Wei,Lin, Francis,Huang, Zheng-Yu,Lin, Hao-Wu,Wang, Po-Han,Liu, Yi-Hung,Wong, Ken-Tsung,Wen, Jianguo,Miller, Dean J.,Darling, Seth B.. "Vacuum-deposited small-molecule organic solar cells with high power conversion efficiencies by judicious molecular design and device optimization". scheme or table. p. 13616 - 13623. Retrieved 2012/10/08.