4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane
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CAS No. 680596-79-6
Cat. No. CS-W009082
Molecule weight266.14
Purity≥98%
MDL No.MFCD04115656

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4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane|CS-W009082

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General Information

CAS No. 680596-79-6
Cat. No. CS-W009082
Purity ≥98%
MDL No. MFCD04115656
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₃BO₄
Molecular Weight 266.14
Synonym(s) 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID, PINACOL ESTER
SMILES CC1(C)OB(C(CC2)=CCC32OCCO3)OC(C)1C

Description

This boronate ester features a spirocyclic dioxolane framework that enhances stability and facilitates efficient coupling in Suzuki-Miyaura reactions. The tetramethyl substitution reduces hydrolytic sensitivity, while the 1,4-dioxaspiro[4.5]dec-7-en-8-yl moiety enables selective functionalization under mild conditions.

Application

This boronate ester serves as a stable, bench-ready building block for Suzuki-Miyaura coupling reactions. The spirocyclic dioxaborolane framework enhances thermal stability and minimizes protodeboronation, enabling reliable cross-coupling with aryl and vinyl halides under mild conditions. Its orthogonal reactivity profile facilitates sequential functionalization in complex molecule synthesis, making it a practical choice for constructing heterocyclic scaffolds and advanced intermediates in medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  170011-47-9
- ~93%
- In-stock
  
  680596-79-6
References
- US2010/56576 A1, ; Page/Page column 20 ; US 20100056576 A1
Route2
- 25015-63-8
- In-stock
  
  170011-47-9
- ~%
- In-stock
  
  680596-79-6
References
- US2006/3997 A1, ; Page/Page column 7 ;

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

TPSA 36.92
LogP 2.4712
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Dioxolane compounds

Building Blocks Skeleton Spirol Rings compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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4,4,5,5-Tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane

CAS No. 680596-79-6

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