3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopent-2-en-1-one

Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopent-2-en-1-one
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CAS No. 1370008-65-3
Cat. No. CS-0051753
Purity≥95%
MDL No.MFCD22683474

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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopent-2-en-1-one|CS-0051753

Structure of 1370008-65-3

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Description

This boronate ester integrates a cyclopentenone scaffold with a tetramethyl-1,3,2-dioxaborolane moiety, enabling direct functionalization via Suzuki-Miyaura coupling. The electron-deficient enone system enhances reactivity in cross-coupling protocols, while the stable dioxaborolane group ensures compatibility with aqueous and oxidative conditions. This structure facilitates rapid access to substituted cyclopentenones under standard bench protocols.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopent-2-en-1-one serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The cyclopentenone core provides a versatile scaffold for heterocyclic and natural product synthesis, with the tetramethylboronate group offering excellent functional group tolerance and predictable reactivity under standard catalytic conditions. Its crystalline nature facilitates purification and handling, enabling efficient integration into multi-step synthetic sequences.

General Information

CAS No. 1370008-65-3
Cat. No. CS-0051753
Purity ≥95%
MDL No. MFCD22683474
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₇BO₃
Molecular Weight 208.06
Synonym(s) 2-Cyclopenten-1-one, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
SMILES CC1(C)OB(OC1(C)C)C1=CC(=O)CC1

Computational Chemistry Data

TPSA 35.53
LogP 1.9071
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

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 Ketone

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopent-2-en-1-one

CAS No. 1370008-65-3

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