3-Hexylthiophene Chemical Properties

Melting point:

-39.15°C (estimate)

Boiling point:

65 °C/0.45 mmHg (lit.)

Density 

0.936 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.496(lit.)

Flash point:

100 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Liquid

color 

Clear colorless to slightly yellow or red

Water Solubility 

Partly soluble in water.

BRN 

1617129

InChI

InChI=1S/C10H16S/c1-2-3-4-5-6-10-7-8-11-9-10/h7-9H,2-6H2,1H3

InChIKey

JEDHEMYZURJGRQ-UHFFFAOYSA-N

SMILES

C1SC=CC=1CCCCCC

CAS DataBase Reference

1693-86-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

10-20/21/22-36/37/38-20

Safety Statements 

16-26-36-37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-Hexylthiophene Usage And Synthesis

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%.

Chemical Properties

colorless transparent or light yellow liquid

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.

Uses

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).

Preparation

The 2,5-dibromo-3-dodecylthiophene was dissolved in tetrahydromyran, added with methylmagnesium bromide, preheated and added with catalyst for reaction reaction was injected into alcohol solvent, and hexane was added to remove the copolymer, and then the mixture was soxhlet filtered using chloroform, and the chloroform layer was evaporated and concentrated to obtain a purple membrane; the purple membrane was vacuum filtered to obtain the product 3-hexylthiophene.

General Description

3-Hexylthiophene, a sulfur containing heterocyclic building block, is a thiophene derivative. Poly(3-hexylthiophene) (P3HT) nanofibres have been used for the preparation of organic phototransistors (OPTs).

Synthesis

The general procedure for the synthesis of 3-hexylthiophene from 3-bromothiophene and hexylmagnesium bromide via a nickel-catalyzed coupling reaction was as follows: 3-bromothiophene (166.0 g, 1.018 mol) and anhydrous diethyl ether (300 mL) were added to a three-necked flask equipped with a stirrer under the protection of nitrogen gas, and then Ni(dppp)Cl2 catalyst (5.19 g, 0.0102 mol). The reaction system was cooled to 0 °C and a 2.0 M diethyl ether solution of hexylmagnesium bromide (0.61 L, 1.22 mol) was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction mixture was neutralized with 1 M HCl solution, followed by extraction of the organic phase with ether. The organic phase was washed with saturated NaHCO3 solution and dried with MgSO4. The dried organic phase was purified by short distillation to afford 3-hexylthiophene (163.73 g, 0.973 mol, 95.6% yield) with a boiling point of 81-84 °C (7.103 mbar). The product was characterized by TLC (unfolding agent: hexane, Rf = 0.81), 1H NMR, 13C NMR, GC/MS and FT-IR.

References

[1] Patent: WO2010/504, 2010, A1. Location in patent: Page/Page column 25-26
[2] Patent: WO2011/69554, 2011, A1. Location in patent: Page/Page column 28-29
[3] New Journal of Chemistry, 2001, vol. 25, # 2, p. 318 - 321
[4] Journal of Organic Chemistry, 2002, vol. 67, # 14, p. 4924 - 4936
[5] Angewandte Chemie - International Edition, 2009, vol. 48, # 43, p. 8014 - 8017

3-Hexylthiophene(1693-86-3)Related Product Information

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• Tetrahydrothiophene
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• Cephalothin sodium
• Thiophene
• 3-Decylthiophene
• 3-Octylthiophene
• 2,5-DIBROMO-3-DODECYLTHIOPHENE
• POLYTHIOPHENE
• Poly(3-hexylthiophene-2,5-diyl)
• 3-N-HEPTYLTHIOPHENE
• 2,5-Dibromo-3-octylthiophene
• 3-DODECYLTHIOPHENE
• 2,5-DIBROMO-3-DECYLTHIOPHENE
• 3-N-NONYLTHIOPHENE
• 3-N-UNDECYLTHIOPHENE
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