4,4,5,5-Tetramethyl-2-(4-methylnaphthalen-1-yl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(4-methylnaphthalen-1-yl)-1,3,2-dioxaborolane
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CAS No. 627526-50-5
Cat. No. CS-0061329
Purity≥97%
MDL No.None

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4,4,5,5-Tetramethyl-2-(4-methylnaphthalen-1-yl)-1,3,2-dioxaborolane|CS-0061329

Structure of 627526-50-5

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General Information

CAS No. 627526-50-5
Cat. No. CS-0061329
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₇H₂₁BO₂
Molecular Weight 268.16
Synonym(s) 4-Methylnaphthalene-1-boronic acid, pinacol ester
SMILES CC1=CC=C(C2=CC=CC=C12)B3OC(C)(C)C(C)(C)O3

Description

This boronate ester integrates a sterically shielded tetramethylcyclopentadienyl core with a 4-methylnaphthalen-1-yl group, enabling stable coupling in Suzuki-Miyaura reactions. The electron-rich naphthyl moiety enhances reactivity while the bulky methyl substituents confer moisture tolerance and bench stability under standard conditions.

Application

4,4,5,5-Tetramethyl-2-(4-methylnaphthalen-1-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its naphthyl moiety enables efficient construction of biaryl scaffolds with enhanced solubility and thermal stability. The tetramethyl-substituted dioxaborolane ring ensures high functional group tolerance and minimal protodeboronation, facilitating reliable coupling under standard conditions. This reagent functions effectively in late-stage diversification and heterocyclic synthesis 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-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 18.46
LogP 3.44742
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Key Words

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4,4,5,5-Tetramethyl-2-(4-methylnaphthalen-1-yl)-1,3,2-dioxaborolane

CAS No. 627526-50-5

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