2-(Dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(Dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 912824-84-1
Cat. No. CS-0091612
Purity≥97%
MDL No.MFCD18452170

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2-(Dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0091612

Structure of 912824-84-1

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General Information

CAS No. 912824-84-1
Cat. No. CS-0091612
Purity ≥97%
MDL No. MFCD18452170
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₁₉BO₂S
Molecular Weight 310.22
Synonym(s) 4-Dibenzothiopheneboronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C2=C3C(C4=CC=CC=C4S3)=CC=C2)O1

Description

This boronate ester features a dibenzo[b,d]thiophene core, offering enhanced stability and reactivity in Suzuki-Miyaura cross-coupling reactions. The tetramethyl-substituted dioxaborolane ring ensures excellent shelf life and moisture tolerance, enabling reliable use under standard conditions.

Application

2-(Dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its dibenzo[b,d]thiophene moiety imparts structural rigidity and electron-rich character, enabling efficient coupling with aryl halides and triflates under mild conditions. The tetramethyl-substituted dioxaborolane enhances shelf stability and facilitates purification, making it ideal for constructing complex heteroaromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  76-09-5
- In-stock
  
  108847-20-7
- ~%
- In-stock
  
  912824-84-1
References
- Fier, Patrick S.; Luo, Jingwei; Hartwig, John F. Journal of the American Chemical Society, 2013 , vol. 135, # 7 p. 2552 - 2559

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 18.46
LogP 4.3537
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Benzothiophene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Benzothiophenes

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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2-(Dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 912824-84-1

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