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Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate

  • CAS No. 151075-20-6

  • Cat. No. CS-W006636
  • Purity≥96%
  • MDL No.MFCD11520532

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

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate|CS-W006636

Structure of 151075-20-6

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General Information

  • CAS No. 151075-20-6
  • Cat. No. CS-W006636
  • Purity ≥96%
  • MDL No. MFCD11520532
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₃BO₄
  • Molecular Weight 266.14
  • Synonym(s) 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3-CYCLOHEXENE-1-CARBOXYLIC ACID METHYL ESTER
  • SMILES CC1(C)C(C)(C)OB(C2=CCC(C(OC)=O)CC2)O1

Description

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate features a boronate ester group integrated into a cyclohexenyl framework, enabling efficient Suzuki-Miyaura coupling. The tetramethyl-substituted dioxaborolane moiety ensures excellent stability and moisture tolerance. This reagent facilitates the construction of complex carbocyclic architectures under mild conditions.

Application

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate serves as a versatile boron building block for Suzuki-Miyaura cross-coupling reactions. The stabilized boronate ester exhibits excellent bench stability and tolerates a range of functional groups, enabling efficient construction of substituted cyclohexene scaffolds. Its compatibility with standard coupling conditions facilitates reliable access to complex molecular architectures in medicinal chemistry and materials 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

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Computational Chemistry Data

  • TPSA   44.76
  • LogP   2.5173
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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