2,5-Bis-Thiopheneboronic acid pinacol ester Chemical Properties

Melting point:

216-220℃

Boiling point:

434.3±30.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

form 

powder

color 

White to Almost white

InChI

InChI=1S/C16H26B2O4S/c1-13(2)14(3,4)20-17(19-13)11-9-10-12(23-11)18-21-15(5,6)16(7,8)22-18/h9-10H,1-8H3

InChIKey

AOJXAKMKFDBHHT-UHFFFAOYSA-N

SMILES

C1(B2OC(C)(C)C(C)(C)O2)SC(B2OC(C)(C)C(C)(C)O2)=CC=1

Safety Information

WGK Germany 

3

HS Code 

2934999090

2,5-Bis-Thiopheneboronic acid pinacol ester Usage And Synthesis

Uses

Diboronic acid ester thiophene monomer for polymerization by Suzuki coupling; used for OPV and OFET applications.

Synthesis

To a solution of 2,5-dibromothiophene (2.0 g, 8.3 mmol) in anhydrous THF (40 mL) was slowly added n-butyllithium (n-BuLi, 15 mL, 1.6 M hexanes solution, 25 mmol) dropwise at -78 °C and the reaction mixture was stirred for 1 hour keeping the temperature at -78 °C. Subsequently, tributyl borate (6.4 mL, 25 mmol) was added to the reaction mixture at the same temperature and the reaction system was gradually warmed to room temperature. After continued stirring for 2 hours, pinacol (3.8 g, 33 mmol) and acetic acid (1.4 mL, 25 mmol) were added sequentially and the resulting mixture was stirred and reacted for 14 hours at room temperature. After completion of the reaction, the reaction solution was filtered through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The residue (brown solid) was purified by recrystallization from a solvent mixture of ethyl acetate and hexane to afford the target product dipinacol ester of thiophene-2,5-diboronic acid (2.0 g, 75% yield) as a white solid.

References

[1] Chem, 2016, vol. 1, # 1, p. 91 - 101

2,5-Bis-Thiopheneboronic acid pinacol ester(175361-81-6)Related Product Information

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• Ethyl thiophene-3-carboxylate
• 2-Hydroxythiophene
• Thiophene-3-boronic acid pinacol ester
• THIENO[3,2-B]PYRIDINE
• Thiophene-2,3-dicarboxylic acid
• THIOPHENE-2-THIOCARBOXAMIDE
• Pseudothiohydantoin
• Thiazolyl Blue
• Dimethyl thiophene-2,3-dicarboxylate
• THIENO(3 2-B)PYRIDIN-7-OL
• Bis(pinacolato)diboron
• 3,5-Bis(trifluoromethyl)benzeneboronic acid
• 2,4-Bis(trifluoromethyl)phenylboronic acid
• 2,4-Bis(trifluoromethyl)benzeneboronic acid pinacol ester
• 3,4-Bis(trifluoroMethyl)phenylboronic acid
• 2,5-BIS(TRIFLUOROMETHYL)BENZENEBORONIC ACID
• 2,5-THIOPHENEDIBORONIC ACID