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CS-W001157 4
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4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane

  • CAS No. 165904-22-3

  • Cat. No. CS-0174174
  • Purity≥98%
  • MDL No.None

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

4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane|CS-0174174

Structure of 165904-22-3

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General Information

  • CAS No. 165904-22-3
  • Cat. No. CS-0174174
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₁BO₂
  • Molecular Weight 232.13
  • Synonym(s) 4,4,5,5-tetraMethyl-2-(2-phenylethyl)-1,3,2-dioxaborolane
  • SMILES CC1(C(C)(OB(O1)CCC2=CC=CC=C2)C)C

Description

This boronate ester features a phenethyl-substituted dioxaborolane core, offering enhanced stability and moisture tolerance. It integrates readily into Suzuki-Miyaura coupling reactions under standard conditions, enabling efficient C–C bond formation with aryl halides. The tetramethyl substitution minimizes side reactivity while maintaining high functional group compatibility.

Application

4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent for Suzuki-Miyaura cross-coupling reactions. Its phenethyl group provides direct access to biaryl architectures common in pharmaceutical intermediates, while the tetramethyl substitution enhances shelf stability and minimizes protodeboronation. The dioxaborolane moiety facilitates efficient coupling with aryl halides under mild conditions, enabling predictable C–C bond formation with broad functional group tolerance.

Synthesis

  • Route1
    • null|null
      292638-84-7
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~97%
    • In-stock
      4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane|CS-0174174
      165904-22-3

    References

    • Cano, Rafael; Ramon, Diego J.; Yus, Miguel Journal of Organic Chemistry, 2010 , vol. 75, # 10 p. 3458 - 3460
  • Route2
    • 2-(1-Chloro-2-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-1145886
      1259299-79-0
    • ~0%
    • null|null
      1259299-92-7
    • In-stock
      4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane|CS-0174174
      165904-22-3

    References

    • Roseblade, Stephenj.; Casas-Arce, Eva; Nettekoven, Ulrike; Gazic Smilovic, Ivana; Zanotti-Gerosa, Antonio; Casar, Zdenko Synthesis (Germany), 2013 , vol. 45, # 20 art. no. SS-2013-Z0439-PSP, p. 2824 - 2831
  • Route3
    • null|null
      292638-84-7
    • null|null
      25015-63-8
    • ~96%
    • In-stock
      4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane|CS-0174174
      165904-22-3

    References

    • Crudden, Cathleen M.; Hleba, Yonek B.; Chen, Austin C. Journal of the American Chemical Society, 2004 , vol. 126, # 30 p. 9200 - 9201

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.3213
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   3

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