2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 859217-67-7
Cat. No. CS-0101262
Purity≥97%
MDL No.MFCD08690233

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2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0101262

Structure of 859217-67-7

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General Information

CAS No. 859217-67-7
Cat. No. CS-0101262
Purity ≥97%
MDL No. MFCD08690233
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₅BO₂
Molecular Weight 236.16
Synonym(s) 4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER
SMILES CC1(C(C)(OB(O1)C2=CCC(C)(CC2)C)C)C

Description

This boronate ester features a sterically shielded tetramethyl-1,3,2-dioxaborolane ring paired with a cyclohexenyl substituent, delivering enhanced stability and reactivity in Suzuki-Miyaura coupling. The dimethylcyclohexenyl group imparts rigidity and improved solubility, enabling efficient cross-coupling under mild conditions.

Application

2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its sterically protected boronate moiety exhibits excellent functional group tolerance and reactivity with aryl, vinyl, and heteroaryl halides. The cyclohexenyl substituent provides a rigid, hydrophobic scaffold useful in medicinal chemistry and materials synthesis, while the tetramethyl substitution enhances air stability and simplifies purification.

Synthesis

Route1
- 98056-47-4
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  859217-67-7
References
- US2005/261291 A1, ; Page/Page column 53 ;
Route2
- 61676-62-8
- 64692-81-5
- ~52%
- In-stock
  
  859217-67-7
References
- Wang, Heng-Yen; Anderson, Laura L. Organic Letters, 2013 , vol. 15, # 13 p. 3362 - 3365

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 3.7543
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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2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 859217-67-7

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