1,3,5-Tri(thiophen-2-yl)benzene

Base Information

• Chemical Name: 1,3,5-Tri(thiophen-2-yl)benzene
• CAS No.: 15509-95-2
• Molecular Formula: C18H12S3
• Molecular Weight: 324.491
• Hs Code.: 2934999090
• European Community (EC) Number: 695-506-7
• DSSTox Substance ID: DTXSID80399545
• Nikkaji Number: J624.393B
• Wikidata: Q82202175
• Mol file: 15509-95-2.mol

Synonyms:1,3,5-Tri(thiophen-2-yl)benzene;15509-95-2;1,3,5-Tri(2-thienyl)benzene;1,3,5-Tris(2-thienyl)benzene;2-(3,5-dithiophen-2-ylphenyl)thiophene;Thiophene, 2,2',2''-(1,3,5-benzenetriyl)tris-;1,3,5-tristhienyl-benzene;SCHEMBL4338418;YSZC1291;DTXSID80399545;MFCD02323391;AKOS016007050;2-[3,5-di(2-thienyl)phenyl]thiophene;1,3,5-Tris(2-thienyl)benzene, 97%;AC-27852;CS-0110379;T2866;T71845;AC-776/15493006

Chemical Property of 1,3,5-Tri(thiophen-2-yl)benzene

Chemical Property:

• Melting Point: 157.0 to 161.0 °C
• Boiling Point: 298°C/10mmHg(lit.)
• PSA: 84.72000
• LogP: 6.87210
• Solubility.: soluble in Toluene
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 324.01011390
• Heavy Atom Count: 21
• Complexity: 281

Purity/Quality:

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

1,3,5-Tri(2-thienyl)benzene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=CC(=CC(=C2)C3=CC=CS3)C4=CC=CS4
• Uses: 1,3,5-Tris(2-thienyl)benzene is a trifunctionalized monomer that can be used in the synthesis of conjugated C3-symmetric poly(arylbenzene) polymers. These polymeric materials can further be used in organic photovoltaic devices as well as organic field effect transistors (OFETs) and organic light emitting diodes (OLED) systems.

Technology Process of 1,3,5-Tri(thiophen-2-yl)benzene

There total 17 articles about 1,3,5-Tri(thiophen-2-yl)benzene 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: 98.0%

2-(2-nitroethenyl)thiophene (874-84-0,34312-77-1) → 1,3,5-tris(2-thienyl)benzene (15509-95-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 0.25h; Sealed tube;

DOI:10.1002/ejoc.201801290

Reference yield: 93.0%

1,3,5-trisbromobenzene (626-39-1) + tributyl(thien-2-yl)stannane (54663-78-4) → 1,3,5-tris(2-thienyl)benzene (15509-95-2)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 12h; Inert atmosphere; Reflux;

Reference yield: 91.0%

thiophene boronic acid (6165-68-0) + 1,3,5-trisbromobenzene (626-39-1) → 1,3,5-tris(2-thienyl)benzene (15509-95-2)

Guidance literature:

With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate; In tetrahydrofuran; water; for 48h; Inert atmosphere; Reflux;

DOI:10.1002/asia.201700890

upstream raw materials:

2-(2-nitroethenyl)thiophene

1,3,5-trisbromobenzene

2-thienylzinc chloride

2-Acetylthiophene

Downstream raw materials:

C₅₄H₉₀S₃Sn₃

Refernces

• 1、 Dong, Yujie,Luo, Feifei,Chen, Lan,Yuan, Feiya,Hou, Yuejiao,Li, Weijun,Yan, Shuanma,Dai, Yuyu,Ouyang, Mi,Zhang, Cheng. "Multi-color electrochromism containing green color based on electrochemically polymerized star-shaped phenyl bithiophene". . p. 12923 - 12928. Retrieved 2018.
• 2、 Li, Weijun,Luo, Feifei,Zhang, Ling,Yan, Shuanma,Zhao, Ruiyang,Ren, Ning,Wu, Yizhao,Chen, Yuliang,Dong, Yujie,Ouyang, Mi,Zhang, Cheng. "Synthesis, electrochemistry, and electrochromic properties of branched thiophene polymers with different conjugation lengths". . p. 2340 - 2348. Retrieved 2019.
• 3、 Wagh, Ganesh D.,Akamanchi, Krishnacharya G.. "Sulfated tungstate catalyzed synthesis of C3-symmetric 1,3,5-triaryl benzenes under solvent-free condition". . p. 3032 - 3036. Retrieved 2017.
• 4、 Zhang, Shanlin,Jiang, Bo,Zhan, Chuanlang,Huang, Jianhua,Zhang, Xin,Jia, Hui,Tang, Ailing,Chen, Lili,Yao, Jiannian. "Phenyl-1,3,5-trithienyl-diketopyrrolopyrrole: A molecular backbone potentially affording high efficiency for solution-processed small-molecule organic solar cells through judicious molecular design". . p. 2407 - 2416. Retrieved 2013.
• 5、 Yang, Kai,Wang, Pengfei,Sun, Ze-Ying,Guo, Minjie,Zhao, Wentao,Tang, Xiangyang,Wang, Guangwei. "Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes". supporting information. p. 3933 - 3938. Retrieved 2021/05/26.