3-Hexylthiophene

Base Information

• Chemical Name: 3-Hexylthiophene
• CAS No.: 1693-86-3
• Molecular Formula: C10H16S
• Molecular Weight: 168.303
• Hs Code.: 29349990
• European Community (EC) Number: 629-237-3
• DSSTox Substance ID: DTXSID20340733
• Nikkaji Number: J256.577C
• Wikidata: Q72482430
• Mol file: 1693-86-3.mol

Synonyms:3-Hexylthiophene;1693-86-3;3-n-Hexylthiophene;Thiophene, 3-hexyl-;MFCD00143181;3-hexylthiophen;3-hexyl-thiophene;SCHEMBL27647;3-Hexylthiophene, >=99%;DTXSID20340733;BBL102713;GEO-01495;STL556519;AKOS005257744;AC-4501;AM84585;CS-W004388;SB66471;AS-19031;FT-0600389;FT-0615787;H0756;EN300-95564;Q-100204

Chemical Property of 3-Hexylthiophene

Chemical Property:

• Appearance/Colour: colorless transparent or light yellow liquid
• Vapor Pressure: 0.128mmHg at 25°C
• Melting Point: -39.15°C (estimate)
• Refractive Index: n20/D 1.496(lit.)
• Boiling Point: 225.6 °C at 760 mmHg
• Flash Point: 64.2 °C
• PSA: 28.24000
• Density: 0.946 g/cm³
• LogP: 3.87090
• Storage Temp.: Flammables area
• Water Solubility.: Partly soluble in water.
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 168.09727168
• Heavy Atom Count: 11
• Complexity: 90.9

Purity/Quality:

99% ^*data from raw suppliers

3-Hexylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 10-20/21/22-36/37/38-20
• Safety Statements: 16-26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCC1=CSC=C1
• Description: 3-Hexylthiophene is the intermediate for the synthesis of poly(3-hexylthiophene), referred as P3HT. To date, it is the most studied polymer for polymer solar cells. The efficiency of a P3HT/PCBM solar cell is typically 4-5 %, but with new fullerene materials developed to closely match the energy levels of P3HT (HOMO 5.0 eV, LUMO 3.0 eV), device performances have been pushed to 6.5%.
• Uses: 3-n-Hexylthiophene is a conducting polymer precursor. may be used in the synthesis of poly(3-hexylthiophene). MgKR X-ray and low energy electron induced oligomerization of physisorbed layers of 3-hexylthiophene condensed on clean gold results in the formation of an organic film. 3-Hexylthiophene may be used as starting reagent in the synthesis of poly(3-hexylthiophene) (P3HT). Poly(3-hexylthiophene) (P3HT) nanofibres have been used for the preparation of organic phototransistors (OPTs).

Technology Process of 3-Hexylthiophene

There total 24 articles about 3-Hexylthiophene 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: 97.0%

2-bromo-4-n-hexylthiophene (210705-84-3) → 3-hexylthiophene (1693-86-3)

Guidance literature:

2-bromo-4-n-hexylthiophene; With magnesium; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With hydrogenchloride; In water; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.06.100

Reference yield: 95.6%

3-Bromothiophene (872-31-1) + n-hexylmagnesium bromide (3761-92-0) → 3-hexylthiophene (1693-86-3)

Guidance literature:

1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; at 0 - 20 ℃; Inert atmosphere;

Reference yield: 87.0%

3-Bromothiophene (872-31-1) + 1-bromo-hexane (111-25-1) → 3-hexylthiophene (1693-86-3)

Guidance literature:

1-bromo-hexane; With magnesium; In diethyl ether; at 0 ℃; for 2h; Inert atmosphere;

3-Bromothiophene; With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; at 20 ℃; Inert atmosphere;

DOI:10.1021/ma4007945

upstream raw materials:

3-Bromothiophene

1-bromo-hexane

Trihexylboran; Tri-n-hexylbor

3-hexyl-2-bromothiophene

Downstream raw materials:

2,5-dibromo-3-hexylthiophene

(4-hexylthiophen-2-yl)boronic acid

3,4'-dihexyl-2,2'-bithiophene

2-[5-(tert-butyldimethylsilanyl)]-[3-(n-hexyl)thiophen-2-yl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Refernces

• 1、 Kuila, Biplab K.,Nandi, Arun K.. "Physical, mechanical, and conductivity properties of poly(3-hexylthiophene) -montmorillonite clay nanocomposites produced by the solvent casting method". . p. 8577 - 8584. Retrieved 2004.
• 2、 Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang. "Redox-Divergent Construction of (Dihydro)thiophenes with DMSO". supporting information. p. 24284 - 24291. Retrieved 2021/10/08.
• 3、 Dilchert, Katharina,Gessner, Viktoria H.,Gro?johann, Angela,Rodstein, Ilja,Scherpf, Thorsten,Steinert, Henning,Tappen, Jens. "Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents". supporting information. p. 20596 - 20603. Retrieved 2020/09/09.