5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde

Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde
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CAS No. 1040281-83-1
Cat. No. CS-W000855
Purity≥97%
MDL No.MFCD09266186

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde|CS-W000855

Structure of 1040281-83-1

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General Information

CAS No. 1040281-83-1
Cat. No. CS-W000855
Purity ≥97%
MDL No. MFCD09266186
Storage -20°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₅BO₃S
Molecular Weight 238.11
Synonym(s) 5-Formyl-2-thiopheneboronic Acid Pinacol Ester
SMILES O=Cc1ccc(s1)B1OC(C(O1)(C)C)(C)C

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde delivers a boronate handle flanked by a thiophene ring and an aldehyde group, enabling efficient coupling in Suzuki-Miyaura reactions. The tetramethyl-substituted dioxaborolane enhances stability and moisture tolerance, while the aldehyde functionality supports downstream derivatization. This bifunctional scaffold integrates seamlessly into complex molecular architectures under standard conditions.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The boronate ester group enables efficient C–C bond formation under mild conditions, while the aldehyde functionality provides a handle for further derivatization via oxidation, reduction, or condensation reactions. Bench-stable and compatible with diverse functional groups, it facilitates the synthesis of complex thiophene-based scaffolds relevant to pharmaceutical and materials chemistry.

Synthesis

Route1
- In-stock
  
  4701-17-1
- In-stock
  
  73183-34-3
- ~92%
- In-stock
  
  1040281-83-1
References
- Zhao, Yun; Jiang, Kejian; Xu, Wei; Zhu, Daoben Tetrahedron, 2012 , vol. 68, # 44 p. 9113 - 9118

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

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Computational Chemistry Data

TPSA 35.53
LogP 1.8598
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Material Science Solar Cell Materials Donor Intermediate DI

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

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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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehyde

CAS No. 1040281-83-1

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