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CS-W001157 4
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2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 517874-21-4

  • Cat. No. CS-0094700
  • Purity≥95%
  • MDL No.MFCD05663890

*For research and further manufacturing use only, not for direct human use.

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0094700

Structure of 517874-21-4

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General Information

  • CAS No. 517874-21-4
  • Cat. No. CS-0094700
  • Purity ≥95%
  • MDL No. MFCD05663890
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₉BO₄
  • Molecular Weight 262.11
  • Synonym(s) 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2,3-DIHYDROBENZO-1,4-DIOXOLINE
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(OCCO3)C3=C2)O1

Description

This boronate ester integrates a dihydrobenzodioxin moiety with a tetramethyl-1,3,2-dioxaborolane unit, offering enhanced stability and compatibility in Suzuki-Miyaura cross-coupling reactions. The electron-rich aryl group enables efficient palladium-catalyzed bond formation under mild conditions, while the steric protection around boron minimizes protodeboronation. Ideal for constructing complex biaryl architectures in medicinal chemistry and materials synthesis.

Application

2-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. Its dihydrobenzodioxin moiety provides structural rigidity and metabolic stability, while the tetramethyl-substituted dioxaborolane enhances bench stability and functional group tolerance. This reagent facilitates efficient C–C bond formation under mild conditions, enabling rapid access to biaryl architectures common in pharmaceutical and agrochemical synthesis.

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   36.92
  • LogP   1.757
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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