4-((4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzonitrile

Name: 4-((4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzonitrile
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CAS No. 475250-43-2
Cat. No. CS-W021978
Purity≥97%
MDL No.MFCD18383371

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4-((4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzonitrile|CS-W021978

Structure of 475250-43-2

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Description

4-((4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzonitrile features a boronate ester group flanked by a nitrile-substituted benzyl linker, enabling efficient Suzuki-Miyaura coupling under mild conditions. This bench-stable reagent integrates readily into complex molecular architectures with minimal functional group interference.

Application

4-((4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzonitrile serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. The nitrile group enables downstream functionalization via hydrolysis or reduction, while the stable, bench-ready boronate moiety facilitates efficient coupling with aryl halides and pseudohalides under mild conditions. Its compatibility with diverse functional groups and ease of purification make it a practical choice for constructing biaryl and heterocyclic scaffolds in medicinal chemistry and materials science.

General Information

CAS No. 475250-43-2
Cat. No. CS-W021978
Purity ≥97%
MDL No. MFCD18383371
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₈BNO₂
Molecular Weight 243.11
Synonym(s) (4-CYANOBENZYL)BORONIC ACID PINACOL ESTER
SMILES N#CC1=CC=C(CB2OC(C)(C)C(C)(C)O2)C=C1

Computational Chemistry Data

TPSA 42.25
LogP 2.73218
H_Acceptors 3
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 Functional Group Cyanide/Nitrile

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)methyl)benzonitrile

CAS No. 475250-43-2

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