5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene

Name: 5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene
Brand: ChemScene
Availability: InStock
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CAS No. 239075-02-6
Cat. No. CS-0091654
Purity≥98%
MDL No.MFCD06798112

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5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene|CS-0091654

Structure of 239075-02-6

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General Information

CAS No. 239075-02-6
Cat. No. CS-0091654
Purity ≥98%
MDL No. MFCD06798112
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₈B₂O₄S₂
Molecular Weight 418.19
Synonym(s) 2,2'-Bithiophene-5,5'-diboronic Acid Bis(pinacol) Ester
SMILES CC(O1)(C)C(C)(C)OB1C2=CC=C(C3=CC=C(B4OC(C)(C)C(C)(C)O4)S3)S2

Description

5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene features two boronate ester groups flanking a bithiophene core, enabling efficient Suzuki-Miyaura coupling. This bench-stable, moisture-tolerant reagent integrates seamlessly into conjugated polymer synthesis and functional materials development under standard conditions.

Application

5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene serves as a versatile building block for Suzuki-Miyaura cross-coupling reactions, enabling the efficient construction of conjugated oligothiophenes and functionalized π-systems. The stable boronate ester groups facilitate mild reaction conditions, excellent functional group tolerance, and straightforward purification, making it ideal for applications in organic electronics and materials science.

Synthesis

Route1
- In-stock
  
  76-09-5
- In-stock
  
  492-97-7
- ~84%
- In-stock
  
  239075-02-6
References
- THE UNIVERSITY OF MANCHESTER; INGLESON, Michael James Patent: WO2012/25760 A1, 2012 ; Location in patent: Page/Page column 49-50 ;
Route2
- 61676-62-8
- In-stock
  
  492-97-7
- ~69%
- In-stock
  
  239075-02-6
References
- Li, Yaowen; Li, Zaifang; Wang, Chunyu; Li, Hui; Lu, Hongguang; Xu, Bin; Tian, Wenjing Journal of Polymer Science, Part A: Polymer Chemistry, 2010 , vol. 48, # 13 p. 2765 - 2776
Route3
- In-stock
  
  76-09-5
- In-stock
  
  492-97-7
- ~0%
- In-stock
  
  479719-88-5
- In-stock
  
  239075-02-6
References
- Journal of Organic Chemistry, , vol. 67, # 25 p. 8877 - 8884

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 36.92
LogP 4.075
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Material Science Material Composite Block Semiconducting Polymer Synthetic Building Block

Material Science Solar Cell Materials Donor Intermediate DI

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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5,5'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene

CAS No. 239075-02-6

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