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CS-W001157 4
Total: USD 88.00

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol

  • CAS No. 443776-76-9

  • Cat. No. CS-W000934
  • Purity≥98%
  • MDL No.MFCD09266196

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

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol|CS-W000934

Structure of 443776-76-9

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General Information

  • CAS No. 443776-76-9
  • Cat. No. CS-W000934
  • Purity ≥98%
  • MDL No. MFCD09266196
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₉BO₃
  • Molecular Weight 234.10
  • Synonym(s) Benzenemethanol, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
  • SMILES OCc1cccc(c1)B1OC(C(O1)(C)C)(C)C

Description

This boronate-functionalized benzyl alcohol integrates seamlessly into Suzuki-Miyaura coupling reactions, offering high stability and compatibility with diverse reaction conditions. The tetramethyl-1,3,2-dioxaborolane moiety ensures reliable performance under standard bench protocols, while the pendant hydroxyl group enables further derivatization or incorporation into complex molecular architectures.

Application

(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol serves as a versatile boronate building block in palladium-catalyzed cross-coupling reactions. Its stable dioxaborolane group enables efficient Suzuki-Miyaura coupling with aryl and heteroaryl halides, facilitating the construction of biaryl and extended conjugated scaffolds. The pendant benzyl alcohol functionality offers a handle for further derivatization or incorporation into pharmaceutical intermediates, while the tetramethyl substitution enhances bench stability and minimizes protodeboronation.

Synthesis

  • Route1

    References

    • US2012/309746 A1, ; Page/Page column 50 ; US 20120309746 A1
  • Route2

    References

    • Molecules, , vol. 18, # 10 p. 12346 - 12367
  • Route3

    References

    • Organic Letters, , vol. 15, # 18 p. 4850 - 4853

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   38.69
  • LogP   1.4781
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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