2-(4-(tert-Butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(4-(tert-Butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
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CAS No. 287944-06-3
Cat. No. CS-0101276
Purity≥97%
MDL No.MFCD11520535

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2-(4-(tert-Butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0101276

Structure of 287944-06-3

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General Information

CAS No. 287944-06-3
Cat. No. CS-0101276
Purity ≥97%
MDL No. MFCD11520535
Storage 4°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-(4-TERT-BUTYL-1-CYCLOHEXEN-1-YL)-1,3,2-DIOXABOROLANE
SMILES CC1(C(C)(OB(O1)C2=CCC(CC2)C(C)(C)C)C)C

Description

This boronate ester features a sterically hindered tert-butylcyclohexenyl scaffold, enhancing stability and selectivity in cross-coupling reactions. The tetramethyl-1,3,2-dioxaborolane moiety enables efficient Suzuki-Miyaura coupling under mild conditions, offering robust performance in complex molecule synthesis.

Application

This boronate ester serves as a stable, bench-ready building block for Suzuki-Miyaura cross-coupling reactions. The sterically encumbered tert-butylcyclohexenyl moiety provides enhanced stability and facilitates selective functionalization. Its tetramethyl-1,3,2-dioxaborolane framework ensures excellent air and moisture tolerance, enabling reliable coupling with aryl and vinyl halides under mild conditions. Ideal for constructing complex carbocyclic architectures in medicinal chemistry and materials synthesis.

Synthesis

Route1
- 77412-96-5
- In-stock
  
  73183-34-3
- ~94%
- In-stock
  
  287944-06-3
References
- Takagi, Jun; Takahashi, Kou; Ishiyama, Tatsuo; Miyaura, Norio Journal of the American Chemical Society, 2002 , vol. 124, # 27 p. 8001 - 8006
Route2
- 61676-62-8
- 41780-53-4
- ~77%
- In-stock
  
  287944-06-3
References
- Rauniyar, Vivek; Zhai, Huimin; Hall, Dennis G. Synthetic Communications, 2008 , vol. 38, # 22 p. 3984 - 3995

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-P330-P362+P364-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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2-(4-(tert-Butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 287944-06-3

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