3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone

Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone
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CAS No. 1187055-81-7
Cat. No. CS-0054910
Molecule weight222.09
Purity≥96%
MDL No.None

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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone|CS-0054910

Structure of 1187055-81-7

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General Information

CAS No. 1187055-81-7
Cat. No. CS-0054910
Purity ≥96%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₉BO₃
Molecular Weight 222.09
Synonym(s) 3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-cyclohex-2-enone
SMILES CC1(C)C(C)(C)OB(C(CCC2)=CC2=O)O1

Description

This boronate ester integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, delivering functionalized cyclohexenone scaffolds with high efficiency. The tetramethyl-dioxaborolane moiety ensures stability and compatibility under standard conditions, while the enone functionality provides a reactive handle for further synthetic elaboration.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The cyclohexenone core provides a rigid, electron-deficient enone system that facilitates conjugation and enables subsequent functionalization. Its tetramethyl-substituted dioxaborolane enhances stability and minimizes protodeboronation, while the pendant ketone allows for selective transformations including nucleophilic additions and reductions. This compound enables efficient construction of complex molecular architectures in medicinal chemistry and materials science workflows.

Synthesis

Route1
- 109459-28-1
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  1187055-81-7
References
- AMGEN INC.; ALLEN, Jennifer R.; BOURBEAU, Matthew P.; CHEN, Ning; HU, Essa; KUNZ, Roxanne; RUMFELT, Shannon Patent: WO2010/57121 A1, 2010 ; Location in patent: Page/Page column 150 ; WO 2010/057121 A1

Safety Information

Download SDS

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 35.53
LogP 2.2972
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

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)cyclohex-2-enone

CAS No. 1187055-81-7

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