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
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
Safety
- WGK Germany
- 3
- HS Code
- 2934999090
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.
N-Bromosuccinimide Price
- 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
- Product number
- 776920
- Product name
- Thiophene-2,5-diboronic acid bis(pinacol) ester
- Purity
- 99% (GC)
- Packaging
- 5g
- Price
- $281
- Updated
- 2023/06/20
- 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
- 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
- Product number
- B585413
- Product name
- 2,5-Bis-thiopheneboronicacidpinacolester
- Packaging
- 1g
- Price
- $75
- Updated
- 2021/12/16
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
- 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