2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
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CAS No. 862129-81-5
Cat. No. CS-W019854
Purity≥95%
MDL No.MFCD10700154

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2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W019854

Structure of 862129-81-5

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General Information

CAS No. 862129-81-5
Cat. No. CS-W019854
Purity ≥95%
MDL No. MFCD10700154
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₉BO₂S
Molecular Weight 226.14
Synonym(s) 3,6-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-thiopyran; 4,4,5,5-Tetramethyl-2-(tetrahydro-2H-thiopyran-4-yl)-1,3,2-dioxaborolane
SMILES CC1(C)C(C)(C)OB(C2=CCSCC2)O1

Description

This boronate ester features a thiopyran-based heterocyclic scaffold that enhances solubility and stability under standard conditions. The tetramethyl-substituted dioxaborolane ring enables efficient Suzuki-Miyaura coupling, while the fused thiacycle offers unique electronic modulation for synthetic applications in medicinal chemistry and materials science.

Application

2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The thiopyran-containing moiety provides a versatile heterocyclic scaffold with predictable reactivity and excellent functional group tolerance. Its sterically protected boronate ester enables efficient coupling under mild conditions, facilitating the construction of complex molecular architectures in medicinal chemistry and materials science applications.

Synthesis

Route1
- 181180-42-7
- In-stock
  
  73183-34-3
- ~99%
- In-stock
  
  862129-81-5
References
- ELI LILLY AND COMPANY Patent: WO2005/73206 A1, 2005 ; Location in patent: Page/Page column 14-15 ; WO 2005/073206 A1
Route2
- In-stock
  
  1072-72-6
- ~%
- In-stock
  
  862129-81-5
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 17, # 13 p. 3544 - 3549

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 18.46
LogP 2.6811
H_Acceptors 3
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-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 862129-81-5

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