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Ethyl (Z)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate

  • CAS No. 448212-00-8

  • Cat. No. CS-0147696
  • Molecule weight240.10
  • Purity≥95%
  • MDL No.MFCD30718738

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

Ethyl (Z)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate|CS-0147696

Structure of 448212-00-8

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General Information

  • CAS No. 448212-00-8
  • Cat. No. CS-0147696
  • Purity ≥95%
  • MDL No. MFCD30718738
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₂₁BO₄
  • Molecular Weight 240.10
  • Synonym(s) (Z)-(4-Ethoxy-4-oxo-2-buten-2-yl)boronic Acid Pinacol Ester
  • SMILES C/C(B(O1)OC(C)(C)C1(C)C)=C\C(OCC)=O

Description

Ethyl (Z)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate is a bench-stable boronate ester featuring a stereodefined (Z)-alkene and a pendant ethyl ester. This structure enables direct coupling in palladium-catalyzed cross-coupling reactions, delivering functionalized alkenes with high fidelity. The tetramethyl-substituted dioxaborolane moiety enhances stability and solubility in organic solvents.

Application

Ethyl (Z)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-enoate serves as a stable, bench-ready boron building block for palladium-catalyzed cross-coupling reactions. Its (Z)-configured enoate moiety enables stereoselective incorporation into complex frameworks, while the pinacol boronate group offers excellent functional group tolerance and compatibility with standard Suzuki-Miyaura conditions. Ideal for constructing conjugated systems and heterocyclic scaffolds in medicinal chemistry and materials science 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-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   44.76
  • LogP   2.1272
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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