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(E)-2-(2-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 149777-81-1

  • Cat. No. CS-0080684
  • Purity≥97%
  • MDL No.None

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

(E)-2-(2-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0080684

Structure of 149777-81-1

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General Information

  • CAS No. 149777-81-1
  • Cat. No. CS-0080684
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁BO₃
  • Molecular Weight 260.14
  • Synonym(s) 2-[(E)-2-(2-methoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • SMILES CC1(C)C(C)(C)OB(/C=C/C2=CC=CC=C2OC)O1

Description

This boronate ester features a (E)-configured styryl moiety with a methoxy group at the ortho position, enabling efficient cross-coupling in palladium-catalyzed reactions. The tetramethyl-substituted dioxaborolane ring enhances stability and solubility under standard conditions, facilitating reliable use in synthetic workflows.

Application

(E)-2-(2-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for palladium-catalyzed cross-coupling reactions. Its (E)-configured styryl moiety enables efficient Suzuki-Miyaura coupling with aryl and heteroaryl halides, facilitating the construction of conjugated biaryl systems. The tetramethyl-substituted dioxaborolane ring enhances stability and resistance to protodeboronation, while the methoxy group provides predictable electronic modulation. Ideal for iterative synthesis and late-stage functionalization in medicinal chemistry workflows.

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   27.69
  • LogP   3.3398
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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