2-([2,2'-Bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-([2,2'-Bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 479719-88-5
Cat. No. CS-0091659
Molecule weight292.22
Purity≥95%
MDL No.MFCD04039974

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2-([2,2'-Bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0091659

Structure of 479719-88-5

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General Information

CAS No. 479719-88-5
Cat. No. CS-0091659
Purity ≥95%
MDL No. MFCD04039974
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₇BO₂S₂
Molecular Weight 292.22
Synonym(s) 2,2'-Bithiophene-5-boronic acid pinacol ester
SMILES CC1(C)C(C)(C)OB(C2=CC=C(C3=CC=CS3)S2)O1

Description

This boronate ester integrates a bithiophene moiety with a tetramethyl-substituted dioxaborolane, offering enhanced stability and compatibility in cross-coupling reactions. The electron-rich bithiophene unit enables efficient palladium-catalyzed transformations, while the steric protection from methyl groups minimizes protodeboronation. Designed for reliable performance under standard conditions.

Application

2-([2,2'-Bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. Its bithiophene moiety imparts excellent stability and solubility, enabling efficient coupling with aryl and heteroaryl halides under mild conditions. The tetramethyl-substituted dioxaborolane enhances shelf life and facilitates purification, making it ideal for constructing conjugated materials and functionalized heterocycles in organic electronics and medicinal chemistry applications.

Synthesis

Route1
- 61676-62-8
- In-stock
  
  492-97-7
- ~91%
- In-stock
  
  479719-88-5
References
- Haid, Stefan; Marszalek, Magdalena; Mishra, Amaresh; Wielopolski, Mateusz; Teuscher, Joel; Moser, Jacques-E.; Humphry-Baker, Robin; Zakeeruddin, Shaik M.; Graetzel, Michael; Baeuerle, Peter Advanced Functional Materials, 2012 , vol. 22, # 6 p. 1291 - 1302
Route2
- In-stock
  
  76-09-5
- In-stock
  
  492-97-7
- ~86%
- In-stock
  
  479719-88-5
References
- THE UNIVERSITY OF MANCHESTER; INGLESON, Michael James Patent: WO2012/25760 A1, 2012 ; Location in patent: Page/Page column 47 ;
Route3
- 61676-62-8
- 3480-11-3
- ~51%
- In-stock
  
  479719-88-5
References
- GYEONGSANG NATIONAL UNIVERSITY INDUSTRIAL AND ACADEMIC COLLABORATION FOUNDATION Patent: WO2008/120839 A1, 2008 ; Location in patent: Page/Page column 42-43 ;

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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 3.7758
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Material Science Material Composite Block Small Molecule Semiconductor Synthesis Building Block

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Thiophenes

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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2-([2,2'-Bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 479719-88-5

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