3-Octylthiophene

Base Information

• Chemical Name: 3-Octylthiophene
• CAS No.: 104934-51-2
• Molecular Formula: C₁₂H₂₀S
• Molecular Weight: 196.357
• European Community (EC) Number: 628-784-5
• DSSTox Substance ID: DTXSID40340735
• Nikkaji Number: J236.191D
• Wikidata: Q72497698
• Mol file: 104934-51-2.mol

Synonyms:3-Octylthiophene;65016-62-8;3-n-Octylthiophene;Thiophene, 3-octyl-;MFCD00085281;3-octyl-thiophene;3-Octylthiophene, 97%;BIDD:GT0691;SCHEMBL153908;DTXSID40340735;GEO-02064;AKOS004909492;AC-4929;CS-W004389;FD14056;SB66364;AS-19032;SY036408;FT-0616289;O0213;A834948

Chemical Property of 3-Octylthiophene

Chemical Property:

• Melting Point: 198-211 °C
• PSA: 28.24000
• LogP: 4.65110
• Solubility.: chloroform, methylene chloride, toluene and THF: soluble
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 196.12857181
• Heavy Atom Count: 13
• Complexity: 112

Purity/Quality:

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

Poly(3-octylthiophene-2,5-diyl) regioregular, electronic grade, 99.995% trace metals basis, average Mn ~25,000 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1=CSC=C1
• Uses: It is employed Conducting polymer, rechargeable battery electrodes, electrochromic devices, chemical and optical sensors, light-emitting diodes, microelectrical amplifiers, field-effect transistors and non-linear optical materials. It is also used in organic field-effect transistors and in polymer-based solar cells and p-type polymer semiconductor.

Technology Process of 3-Octylthiophene

There total 11 articles about 3-Octylthiophene 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: 98.2%

3-Bromothiophene (872-31-1) + octylmagnesium bromide (17049-49-9) → 3-octylthiophene (65016-62-8,104934-51-2)

Guidance literature:

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; at 0 - 5 ℃; for 0.25h; Inert atmosphere;

DOI:10.1039/c8ob03077d

Reference yield: 73.0%

3-Bromothiophene (872-31-1) + 1-bromo-octane (111-83-1) → 3-octylthiophene (65016-62-8,104934-51-2)

Guidance literature:

1-bromo-octane; With magnesium; In diethyl ether;

3-Bromothiophene; With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; for 24h; Further stages.; Heating;

DOI:10.1021/jo991359c

Reference yield: 72.0%

3-Bromothiophene (872-31-1) + 1-octyl p-toluenesulfonate (3386-35-4) → 3-octylthiophene (65016-62-8,104934-51-2)

Guidance literature:

3-Bromothiophene; With TurboGrignard; In tetrahydrofuran; at 20 ℃; for 24h;

With (trimethylsilyl)methylmagnesium chloride; zinc(II) iodide; In tetrahydrofuran; at 0 ℃;

1-octyl p-toluenesulfonate; With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 0 - 40 ℃;

DOI:10.1021/ol901610a

upstream raw materials:

3-Bromothiophene

octylmagnesium bromide

1-bromo-octane

3,4-dibromothiophene

Downstream raw materials:

tributyl-(4-octyl-thiophen-2-yl)-stannane

Refernces

• 1、 Barba-Barba, Rodrigo M.,Chammam, Marwa,Ramos-Ortiz, Gabriel,Listunov, Dymytrii,Velusamy, Jayaramakrishnan,Rodriguez, Mario,Carriles, Ramon,Silva, Carlos,Duhayon, Carine,Kauffmann, Brice,Maraval, Valérie,Chauvin, Remi. "Linear and nonlinear optical properties of a quadrupolar carbo-benzene and its benzenic parent: The carbo-merization effect". . . Retrieved 2021.
• 2、 Madera, Justin,Slattery, Megan,Arman, Hadi D.,Tonzetich, Zachary J.. "Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope and mechanistic insights". . . Retrieved 2020.
• 3、 Lee,Kim,Rhee. "Preparation and characterization of ester functionalized poly(3-alkylthiophene)s". . p. 31 - 38. Retrieved 1994.
• 4、 Li, Yaowen,Chen, Yujin,Liu, Xing,Wang, Zhong,Yang, Xiaoming,Tu, Yingfeng,Zhu, Xiulin. "Controlling blend film morphology by varying alkyl side chain in highly coplanar donor-acceptor copolymers for photovoltaic application". . p. 6370 - 6381. Retrieved 2011.
• 5、 Chang, Qing,Cheng, Xiaohong,Ding, Wei,Ma, Tao,Zhang, Lin. "Thiophene-benzothiadiazole based donor–acceptor–donor (D-A-D) bolaamphiphiles, self-assembly and photophysical properties". . . Retrieved 2021/11/03.