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
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CAS No. 479719-88-5
Cat. No. CS-0091659
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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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.

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

Computational Chemistry Data

TPSA 18.46
LogP 3.7758
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Safety Information

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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

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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

Key Words

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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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