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

Name: 4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolane
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CAS No. 859217-85-9
Cat. No. CS-W022039
Molecule weight264.21
Purity≥98%
MDL No.MFCD16659018

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4,4,5,5-Tetramethyl-2-(3,3,5,5-tetramethylcyclohex-1-en-1-yl)-1,3,2-dioxaborolane|CS-W022039

Structure of 859217-85-9

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General Information

CAS No. 859217-85-9
Cat. No. CS-W022039
Purity ≥98%
MDL No. MFCD16659018
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₉BO₂
Molecular Weight 264.21
Synonym(s) 4,4,5,5-tetraMethyl-2-(3,3,5,5-tetraMethylcyclohex-1-enyl)-1,3,2-dioxaborolane
SMILES CC1(C)CC(C)(C)C=C(B2OC(C)(C)C(C)(C)O2)C1

Description

This boronate ester features a sterically shielded dioxaborolane ring paired with a bulky cyclohexenyl substituent, enhancing stability and resistance to protodeboronation. It integrates seamlessly into Suzuki-Miyaura coupling reactions under mild conditions, delivering high functional group tolerance and predictable reactivity.

Application

This boronate ester serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. Its sterically encumbered structure enhances hydrolytic stability and functional group tolerance, enabling reliable coupling with aryl and vinyl halides under mild conditions. The tetramethylcyclohexenyl moiety imparts high crystallinity and ease of purification, making it ideal for iterative synthesis of complex molecular architectures in medicinal chemistry and materials science applications.

Synthesis

Route1
- 86544-77-6
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  859217-85-9
References
- US2005/261291 A1, ; Page/Page column 61 ;
Route2
- 61676-62-8
- 42449-09-2
- ~87%
- In-stock
  
  859217-85-9
References
- Rauniyar, Vivek; Zhai, Huimin; Hall, Dennis G. Synthetic Communications, 2008 , vol. 38, # 22 p. 3984 - 3995

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 18.46
LogP 4.3904
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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

CAS No. 859217-85-9

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