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Methyl 2-[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate

  • CAS No. 956229-86-0

  • Cat. No. CS-0049185
  • Purity≥97%
  • MDL No.None

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

Methyl 2-[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate|CS-0049185

Structure of 956229-86-0

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General Information

  • CAS No. 956229-86-0
  • Cat. No. CS-0049185
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁BO₄
  • Molecular Weight 276.14
  • Synonym(s) Methyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
  • SMILES COC(=O)CC1=C(C=CC=C1)B1OC(C)(C)C(C)(C)O1

Description

Methyl 2-[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate features a boronate ester group conjugated to a phenylacetic acid methyl ester scaffold. This structure enables efficient Suzuki-Miyaura cross-coupling reactions under mild conditions. The tetramethylboronate moiety imparts enhanced stability and solubility in organic solvents, facilitating handling and integration into complex synthetic sequences.

Application

Methyl 2-[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pinacol boronate ester group enables efficient C–C bond formation under mild conditions, with excellent functional group tolerance and bench stability. It facilitates the construction of biaryl and substituted phenyl motifs common in pharmaceutical and agrochemical scaffolds, offering reliable yields and straightforward purification.

Synthesis

  • Route1
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    • ~%
    • In-stock
      Methyl 2-[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate|CS-0049185
      956229-86-0

    References

    • ELI LILLY AND COMPANY; HIPSKIND, Philip Arthur; STEPHENSON, Gregory Alan Patent: US2013/29972 A1, 2013 ; US 20130029972 A1
  • Route2

    References

    • Yougnia, Rodrigue; Rochais, Christophe; Oliveira Santos, Jana Sopkova-de; Dallemagne, Patrick; Rault, Sylvain Tetrahedron, 2010 , vol. 66, # 15 p. 2803 - 2808
  • Route3

    References

    • ELI LILLY AND COMPANY; HIPSKIND, Philip Arthur; STEPHENSON, Gregory Alan Patent: US2013/29972 A1, 2013 ; US 20130029972 A1

Safety Information

Download SDS
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   1.7013
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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