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CS-W001157 4
Total: USD 88.00

2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 171364-79-7

  • Cat. No. CS-W003231
  • Purity≥97%
  • MDL No.MFCD05663864

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

2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W003231

Structure of 171364-79-7

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General Information

  • CAS No. 171364-79-7
  • Cat. No. CS-W003231
  • Purity ≥97%
  • MDL No. MFCD05663864
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BO₃
  • Molecular Weight 234.10
  • Synonym(s) 4-Methoxyphenylboronicacidpinacolester
  • SMILES COc1ccc(cc1)B1OC(C(O1)(C)C)(C)C

Description

This boronate ester features a methoxy-substituted phenyl group flanked by tetramethyl-1,3,2-dioxaborolane, delivering enhanced stability and solubility in polar organic solvents. Designed for efficient cross-coupling reactions under standard conditions, it enables reliable C–C bond formation with minimal decomposition.

Application

2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its arylboronate functionality enables efficient C–C bond formation with aryl and vinyl halides under mild conditions, offering excellent functional group tolerance and straightforward purification. The tetramethyl substitution enhances stability and solubility, making it ideal for both small-scale synthesis and scalable process development in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      623-12-1
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~96%
    • In-stock
      2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W003231
      171364-79-7

    References

    • GENENTECH, INC.; SUMITOMO CHEMICAL COMPANY, LIMITED Patent: US2012/123122 A1, 2012 ; Location in patent: Page/Page column 13 ;
  • Route2
    • null|null
      104-94-9
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~74%
    • In-stock
      2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W003231
      171364-79-7

    References

    • PEKING UNIVERSITY Patent: US2012/184768 A1, 2012 ; Location in patent: Page/Page column 2 ;
  • Route3

    References

    • Ratniyom, Jadsada; Dechnarong, Nattanee; Yotphan, Sirilata; Kiatisevi, Supavadee European Journal of Organic Chemistry, 2014 , vol. 2014, # 7 p. 1381 - 1385

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

Quality Control

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Computational Chemistry Data

  • TPSA   27.69
  • LogP   1.9944
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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