3,4-Dihexylthiophene

Base Information

• Chemical Name: 3,4-Dihexylthiophene
• CAS No.: 122107-04-4
• Molecular Formula: C16H28S
• Molecular Weight: 252.45900
• European Community (EC) Number: 878-466-7
• DSSTox Substance ID: DTXSID50571972
• Nikkaji Number: J1.507.472H
• Wikidata: Q82460184
• Mol file: 122107-04-4.mol

Synonyms:3,4-dihexylthiophene;122107-04-4;Thiophene, 3,4-dihexyl-;3,4-Dihexylthiophene, 97%;SCHEMBL3096865;DTXSID50571972;MFCD21363048;AKOS037645167;AS-57946;D4202;T70155

Chemical Property of 3,4-Dihexylthiophene

Chemical Property:

• Refractive Index: n20/D1.494
• Boiling Point: 103°C/0.3mmHg(lit.)
• Flash Point: >110℃
• PSA: 28.24000
• Density: 0.925 g/mL at 25 °C
• LogP: 5.99370
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 252.19117207
• Heavy Atom Count: 17
• Complexity: 149

Purity/Quality:

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

3,4-Dihexylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1=CSC=C1CCCCCC
• Uses: This material is used in the synthesis of donor-acceptor copolymers and low-band gap polymers for use in Organic Photovoltaic Applications. It also has shown to enhance the thermal stability of polythiophene: fullerene solar cells.

Technology Process of 3,4-Dihexylthiophene

There total 2 articles about 3,4-Dihexylthiophene 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%

3,4-dibromothiophene (3141-26-2) + n-hexylmagnesium bromide (3761-92-0) → 3,4-di-n-hexylthiophene (122107-04-4)

Guidance literature:

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether;

DOI:10.1021/ma302005j

Reference yield: 86.0%

3,4-dibromothiophene (3141-26-2) + 1-bromo-hexane (111-25-1) → 3,4-di-n-hexylthiophene (122107-04-4)

Guidance literature:

1-bromo-hexane; With magnesium;

3,4-dibromothiophene; With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether;

DOI:10.1021/ma049371g

Reference yield: 86.0%

3,4-di-n-hexylthiophene (122107-04-4) → 2,5-Dibromo-3,4-dihexylthiophene (151324-67-3)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; acetic acid; for 2h;

DOI:10.1002/(SICI)1521-3765(20000502)6:9<1663::AID-CHEM1663>3.3.CO;2-H

upstream raw materials:

3,4-dibromothiophene

n-hexylmagnesium bromide

1-bromo-hexane

Downstream raw materials:

2,5-Dibromo-3,4-dihexylthiophene

3-(5-((2,6-diphenyl-4H-pyran-4-ylidene)methyl)-3,4-dihexylthiophen-2-yl)-2-cyanoacrylic acid

5-((2,6-diphenyl-4H-pyran-4-ylidene)methyl)-3,4-dihexylthiophene-2-carbaldehyde

Refernces

• 1、 Anthonysamy,Lee,Karunagaran,Ganapathy,Rhee,Karthikeyan,Kim,Ko,Park,Ju,Kim. "Molecular design and synthesis of ruthenium(ii) sensitizers for highly efficient dye-sensitized solar cells". . p. 12389 - 12397. Retrieved 2011.
• 2、 Sivula, Kevin,Luscombe, Christine K.,Thompson, Barry C.,Frechet, Jean M. J.. "Enhancing the thermal stability of polythiophene:fullerene solar cells by decreasing effective polymer regioregularity". . p. 13988 - 13989. Retrieved 2006.
• 3、 -. "Synthesis method of functionally-substituted dicyanoethylene compounds". Paragraph 0068. . Retrieved 2017/08/29.
• 4、 Barik, Satyananda,Navarathne, Daminda,Leborgne, Maxence,Skene. "Conjugated thiophenoazomethines: Electrochromic materials exhibiting visible-to-near-IR color changes". . p. 5508 - 5519. Retrieved 2013/09/12.