4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde

Name: 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde
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CAS No. 1040424-52-9
Cat. No. CS-0174680
Purity≥96%
MDL No.None

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4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde|CS-0174680

Structure of 1040424-52-9

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General Information

CAS No. 1040424-52-9
Cat. No. CS-0174680
Purity ≥96%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₂₁BO₃
Molecular Weight 308.18
Synonym(s) 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzaldehyde
SMILES CC1(C(C)(OB(O1)C2=CC=C(C3=CC=C(C=O)C=C3)C=C2)C)C

Description

4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde is a boronate-functionalized biphenyl aldehyde featuring a stable tetramethyl-1,3,2-dioxaborolane moiety and an aldehyde handle. This reagent integrates readily into Suzuki-Miyaura coupling protocols and enables direct C–C bond formation under mild conditions. The electron-rich biphenyl scaffold enhances reactivity while maintaining bench-stable handling properties.

Application

4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde serves as a versatile Suzuki-Miyaura coupling building block, enabling efficient construction of biaryl aldehyde scaffolds. The boronate ester group exhibits excellent stability and compatibility with diverse reaction conditions, while the aldehyde functionality permits downstream transformations including reductive amination and Wittig olefination. Its bench-stable nature and orthogonal reactivity facilitate streamlined synthesis of complex molecular architectures in medicinal chemistry and materials science workflows.

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

TPSA 35.53
LogP 3.4653
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde

CAS No. 1040424-52-9

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