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Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

  • CAS No. 603122-40-3

  • Cat. No. CS-0153871
  • Purity≥97%
  • MDL No.MFCD06797992

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

Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate|CS-0153871

Structure of 603122-40-3

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General Information

  • CAS No. 603122-40-3
  • Cat. No. CS-0153871
  • Purity ≥97%
  • MDL No. MFCD06797992
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁BO₅
  • Molecular Weight 292.14
  • Synonym(s) Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
  • SMILES CC1(C)C(C)(C)OB(C2=CC(=C(C=C2)C(=O)OC)OC)O1

Description

Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate delivers a boronate ester functionality paired with an electron-rich aromatic core. This bench-stable reagent integrates seamlessly into Suzuki-Miyaura coupling reactions, enabling efficient C–C bond formation under standard conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and minimizes protodeboronation, while the methoxy group fine-tunes electronic properties for predictable reactivity.

Application

Methyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The sterically protected boronate group enables high stability under ambient conditions and facilitates efficient coupling with aryl halides and triflates. Its methoxy and methyl ester functionalities provide orthogonal reactivity for downstream derivatization, making it well-suited for the synthesis of complex aromatic scaffolds in medicinal chemistry and materials science.

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   53.99
  • LogP   1.781
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   3

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