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2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol

  • CAS No. 1294009-05-4

  • Cat. No. CS-0434079
  • Purity≥90%
  • MDL No.None

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

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol|CS-0434079

Structure of 1294009-05-4

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General Information

  • CAS No. 1294009-05-4
  • Cat. No. CS-0434079
  • Purity ≥90%
  • MDL No. None
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₇BO₃
  • Molecular Weight 184.04
  • Synonym(s) 2-(Tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol
  • SMILES OCC(B1OC(C)(C)C(C)(C)O1)=C

Description

This boronate ester features a propenol side chain that enhances solubility and stability in aqueous media. The tetramethyl-substituted dioxaborolane ring ensures excellent shelf life and resistance to hydrolysis. It integrates readily into Suzuki-Miyaura coupling reactions under mild conditions, enabling efficient C–C bond formation with aryl and vinyl halides.

Application

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol serves as a versatile boronate ester building block in palladium-catalyzed cross-coupling reactions. Its vinyl alcohol functionality enables direct incorporation into conjugated systems, while the stabilized dioxaborolane group offers excellent bench stability and compatibility with diverse functional groups. The reagent facilitates efficient Suzuki-Miyaura coupling under mild conditions, enabling rapid assembly of complex molecular architectures with predictable regiochemistry.

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   38.69
  • LogP   1.1663
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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