ChemicalBook > CAS DataBase List > 2,5-Bis-Thiopheneboronic acid pinacol ester

2,5-Bis-Thiopheneboronic acid pinacol ester

Product Name
2,5-Bis-Thiopheneboronic acid pinacol ester
CAS No.
175361-81-6
Chemical Name
2,5-Bis-Thiopheneboronic acid pinacol ester
Synonyms
Thienyl-2,5-diborate;Thiophene-2,5-diboronic acids pinacol ester;2,5-Bis-Thiopheneboronic acid pinacol ester;2,5-Thiophenediboronic acid bis(pinacol) ester;Thiophene-2,5-diboronic acid bis(pinacol) ester;2,5-Bis-thiopheneboronic acid, pinacol ester 98%;Bis(4,4,5,5-tetramethyl-1,3-dioxaborolane)-2,5-thiophene;Thiophene-2,5-diboronic acid bis(pinacol) ester 99% (GC);2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene;2,2'-(2,5-Thiophenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CBNumber
CB51177120
Molecular Formula
C16H26B2O4S
Formula Weight
336.06
MOL File
175361-81-6.mol
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2,5-Bis-Thiopheneboronic acid pinacol ester Property

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
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Safety

WGK Germany 
3
HS Code 
2934999090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
776920
Product name
Thiophene-2,5-diboronic acid bis(pinacol) ester
Purity
99% (GC)
Packaging
1g
Price
$70.6
Updated
2023/06/20
Sigma-Aldrich
Product number
776920
Product name
Thiophene-2,5-diboronic acid bis(pinacol) ester
Purity
99% (GC)
Packaging
5g
Price
$281
Updated
2023/06/20
TCI Chemical
Product number
B5871
Product name
2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$72
Updated
2025/07/31
TCI Chemical
Product number
B5871
Product name
2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$285
Updated
2025/07/31
TRC
Product number
B585413
Product name
2,5-Bis-thiopheneboronicacidpinacolester
Packaging
250mg
Price
$55
Updated
2021/12/16
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2,5-Bis-Thiopheneboronic acid pinacol ester Chemical Properties,Usage,Production

Uses

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

Synthesis

3141-27-3

76-09-5

688-74-4

175361-81-6

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2,5-Bis-Thiopheneboronic acid pinacol ester manufacturers

Career Henan Chemical Co
Product
2,5-Bis-Thiopheneboronic acid pinacol ester 175361-81-6
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
1000KGS
Release date
2019-12-20

175361-81-6, 2,5-Bis-Thiopheneboronic acid pinacol esterRelated Search:

2-Thiopheneboronic acid 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

  • 2,5-Bis-Thiopheneboronic acid pinacol ester
  • Thiophene-2,5-diboronic acid bis(pinacol) ester
  • 2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene
  • 2,5-Thiophenediboronic acid bis(pinacol) ester
  • Bis(4,4,5,5-tetramethyl-1,3-dioxaborolane)-2,5-thiophene
  • Thiophene-2,5-diboronic acids pinacol ester
  • Thiophene-2,5-diboronic acid bis(pinacol) ester 99% (GC)
  • 2,2'-(2,5-Thiophenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane]
  • 4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]-1,3,2-dioxaborolane
  • 2,5-Bis-thiopheneboronic acid, pinacol ester 98%
  • 1,3,2-Dioxaborolane, 2,2'-(2,5-thiophenediyl)bis[4,4,5,5-tetramethyl-
  • Thienyl-2,5-diborate
  • 2,2'-(2,5-Thiophenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • 175361-81-6
  • Thiophene (TH)
  • Organoborons
  • Thiophene