(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)boronic acid

Name: (4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)boronic acid
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CAS No. 162356-89-0
Cat. No. CS-0175375
Purity≥96%
MDL No.None

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(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)boronic acid|CS-0175375

Structure of 162356-89-0

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General Information

CAS No. 162356-89-0
Cat. No. CS-0175375
Purity ≥96%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₃BO₃Si
Molecular Weight 266.22
Synonym(s) 4-TBSMS-hydroxymethylphenylboronic acid
SMILES CC(C)([Si](C)(OCC1=CC=C(B(O)O)C=C1)C)C

Description

This boronate moiety integrates a tert-butyldimethylsilyl-protected hydroxymethyl group, enabling orthogonal functionalization in complex synthesis. The silyl ether stabilizes the benzylic alcohol during reaction sequences, while the boronic acid handles facilitate palladium-catalyzed couplings under mild conditions. This derivative offers enhanced stability and selective deprotection compatibility in multi-step organic transformations.

Application

(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)boronic acid serves as a stable, bench-ready building block for Suzuki-Miyaura couplings, enabling efficient access to biaryl architectures. The silyl ether protects the phenolic hydroxyl during synthesis, offering orthogonal functionality and compatibility with diverse reaction conditions. Its robustness facilitates purification and storage, while the boronic acid group participates reliably in cross-coupling protocols under standard catalytic conditions.

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-P280-P302+P352

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Computational Chemistry Data

TPSA 49.69
LogP 1.8882
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Organosilicon compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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(4-(((Tert-butyldimethylsilyl)oxy)methyl)phenyl)boronic acid

CAS No. 162356-89-0

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