4,4,5,5-Tetramethyl-2-(tetrahydro-2H-pyran-4-yl)-1,3,2-dioxaborolane

Name: 4,4,5,5-Tetramethyl-2-(tetrahydro-2H-pyran-4-yl)-1,3,2-dioxaborolane
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CAS No. 1131912-76-9
Cat. No. CS-W005532
Purity≥95%
MDL No.MFCD11506065

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4,4,5,5-Tetramethyl-2-(tetrahydro-2H-pyran-4-yl)-1,3,2-dioxaborolane|CS-W005532

Structure of 1131912-76-9

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General Information

CAS No. 1131912-76-9
Cat. No. CS-W005532
Purity ≥95%
MDL No. MFCD11506065
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₂₁BO₃
Molecular Weight 212.09
Synonym(s) Tetrahydropyran-4-boronic acid pinacol ester
SMILES CC1(C)OB(OC1(C)C)C1CCOCC1

Description

This boronate ester features a tetrahydro-2H-pyran-4-yl protecting group that enhances stability and solubility in polar organic solvents. It integrates readily into Suzuki-Miyaura cross-coupling reactions under standard conditions, offering reliable performance in complex molecule assembly workflows.

Application

4,4,5,5-Tetramethyl-2-(tetrahydro-2H-pyran-4-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetrahydro-2H-pyran-4-yl group provides orthogonal protection and enhanced solubility, while the tetramethyl-substituted dioxaborolane core ensures high reactivity and resistance to hydrolysis. This compound facilitates efficient coupling with aryl, vinyl, and heteroaryl halides under mild conditions, enabling rapid access to complex molecular architectures in medicinal chemistry and materials synthesis.

Synthesis

Route1
- In-stock
  
  25637-16-5
- In-stock
  
  73183-34-3
- ~53%
- In-stock
  
  1131912-76-9
References
- Yi, Jun; Liu, Jin-Hui; Liang, Jun; Dai, Jian-Jun; Yang, Chu-Ting; Fu, Yao; Liu, Lei Advanced Synthesis and Catalysis, 2012 , vol. 354, # 9 p. 1685 - 1691

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 27.69
LogP 2.2592
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Tetrahydropyran compounds

Key Words

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4,4,5,5-Tetramethyl-2-(tetrahydro-2H-pyran-4-yl)-1,3,2-dioxaborolane

CAS No. 1131912-76-9

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