2,5-Dibromo-3-Dodecylthiophene Chemical Properties

Boiling point:

165°C/0.2mmHg(lit.)

Density 

1.105 g/mL at 25 °C

refractive index 

n20/D 1.509

Flash point:

110 °C

storage temp. 

2-8°C

form 

clear liquid

color 

Colorless to Red to Green

InChIKey

IMILVTHOOISGRW-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HS Code 

29349990

2,5-Dibromo-3-Dodecylthiophene Usage And Synthesis

Chemical Properties

Colorless to yellow liquid

Uses

2-Bromo-3-dodecylthiophene is used in the synthesis of a poly(octathiophene) based copolymer, which is an organic semiconductor that may be used in thin film transistor.

Synthesis

The general procedure for the synthesis of 2-bromo-3-dodecylthiophene using 3-dodecylthiophene as starting material was as follows: a solution of N-bromosuccinimide (NBS) (48 g, 0.27 mol) was prepared by dissolving it in N,N-dimethylformamide (DMF) (160 ml). This solution was added slowly dropwise to a solution of 3-dodecylthiophene (68 g, 0.27 mol) also dissolved in DMF (110 ml). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, 750 ml of water was added to the mixture to quench the reaction. Subsequently, multiple extractions with ether (3 x 300 ml) were performed to separate the organic phase. The combined organic phases were washed sequentially with saturated saline and deionized water, and then dried by adding anhydrous magnesium sulfate to remove residual water. After drying, the solvent was removed by rotary evaporation, and the crude product obtained was subjected to reduced pressure distillation at 125 °C/5 mmHg to finally obtain 2-bromo-3-dodecylthiophene (84.85 g, 94% yield).

References

[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 9, p. 1933 - 1941
[2] Patent: US2010/236631, 2010, A1. Location in patent: Page/Page column 9-10
[3] Journal of the American Chemical Society, 2008, vol. 130, # 27, p. 8580 - 8581
[4] Journal of the American Chemical Society,
[5] Journal of the American Chemical Society, 2009, vol. 131, p. 5586 - 5608

2,5-Dibromo-3-Dodecylthiophene(139100-06-4)Related Product Information

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