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CS-W001157 4
Total: USD 88.00

2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

  • CAS No. 1025707-93-0

  • Cat. No. CS-0097347
  • Molecule weight210.08
  • Purity≥96%
  • MDL No.MFCD07368233

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

2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0097347

Structure of 1025707-93-0

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General Information

  • CAS No. 1025707-93-0
  • Cat. No. CS-0097347
  • Purity ≥96%
  • MDL No. MFCD07368233
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₉BO₃
  • Molecular Weight 210.08
  • Synonym(s) 3,4-Dihydro-2H-pyran-6-boronic acid pinacol ester
  • SMILES CC1(C)C(C)(C)OB(C2=CCCCO2)O1

Description

This boronate ester features a dihydropyran-6-yl moiety that enables selective coupling in Suzuki-Miyaura reactions. The tetramethyl-substituted dioxaborolane ring provides exceptional stability and moisture tolerance, facilitating handling under standard conditions. Ideal for integrating oxygenated heterocycles into complex molecular architectures.

Application

2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura coupling reactions. The dihydropyran moiety provides orthogonal functionality and facilitates downstream transformations in complex molecule synthesis. Its high functional group tolerance and ease of purification make it ideal for iterative cross-coupling strategies in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1
    • null|null
      110-87-2
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • null|null
      121-43-7
    • ~50%
    • In-stock
      2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0097347
      1025707-93-0

    References

    • Butkevich, Alexey N.; Corbu, Andrei; Cossy, Janine; Meerpoel, Lieven; Bonnet, Pascal; Stansfield, Ian; Angibaud, Patrick Organic Letters, 2012 , vol. 14, # 19 p. 4998 - 5001,4
  • Route2

    References

    • Chemistry Letters, , vol. 37, # 6 p. 664 - 665
  • Route3
    • null|null
      110-87-2
    • null|null
      25015-63-8
    • ~%
    • In-stock
      2-(3,4-Dihydro-2H-pyran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0055079
      1046811-99-7
    • In-stock
      2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0097347
      1025707-93-0

    References

    • Bulletin of the Chemical Society of Japan, , vol. 81, # 12 p. 1535 - 1553

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   27.69
  • LogP   2.3121
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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