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CS-W001157 4
Total: USD 88.00

2-Butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 69190-62-1

  • Cat. No. CS-W000962
  • Purity≥98%
  • MDL No.MFCD03789255

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

2-Butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W000962

Structure of 69190-62-1

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General Information

  • CAS No. 69190-62-1
  • Cat. No. CS-W000962
  • Purity ≥98%
  • MDL No. MFCD03789255
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₂₁BO₂
  • Molecular Weight 184.08
  • Synonym(s) But-1-ylboronic acid, pinacol ester
  • SMILES CCCCB1OC(C)(C)C(C)(C)O1

Description

2-Butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane offers enhanced stability and solubility in organic media compared to standard boronate reagents. The sterically shielded tetramethyl substitution minimizes protodeboronation, while the butyl group improves compatibility with diverse reaction conditions. This bench-stable boronate integrates efficiently into Suzuki-Miyaura coupling workflows, enabling reliable C–C bond formation under mild catalytic activation.

Application

2-Butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron reagent enabling efficient Suzuki-Miyaura coupling reactions. Its sterically hindered dioxaborolane core enhances hydrolytic stability and functional group tolerance, facilitating reliable cross-coupling with aryl, heteroaryl, and vinyl halides. The compound functions as a versatile building block in medicinal chemistry and materials synthesis, offering predictable reactivity and straightforward purification.

Synthesis

  • Route1
    • null|null
      280550-84-7
    • ~81%
    • In-stock
      2-Butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W000962
      69190-62-1

    References

    • Walton, John C.; McCarroll, Andrew J.; Chen, Qiao; Carboni, Bertrand; Nziengui, Roger Journal of the American Chemical Society, 2000 , vol. 122, # 23 p. 5455 - 5463
  • Route2
    • null|null
      109-65-9
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~84%
    • In-stock
      2-Butyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-W000962
      69190-62-1

    References

    • Ito, Hajime; Kubota, Koji Organic Letters, 2012 , vol. 14, # 3 p. 890 - 893
  • Route3

    References

    • Pulis, Alexander P.; Aggarwal, Varinder K. Journal of the American Chemical Society, 2012 , vol. 134, # 27 p. 11298 - 11298

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   18.46
  • LogP   2.8787
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   3

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