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CS-W001157 4
Total: USD 88.00

4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane

  • CAS No. 256652-04-7

  • Cat. No. CS-0041414
  • Purity≥97%
  • MDL No.MFCD05663868

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

4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane|CS-0041414

Structure of 256652-04-7

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General Information

  • CAS No. 256652-04-7
  • Cat. No. CS-0041414
  • Purity ≥97%
  • MDL No. MFCD05663868
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₁₉BO₂
  • Molecular Weight 254.13
  • Synonym(s) Naphthalene-2-boronic Acid Pinacol Ester
  • SMILES CC1(C)OB(OC1(C)C)C1=CC2=C(C=CC=C2)C=C1

Description

This boronate moiety integrates a naphthalen-2-yl group with a sterically shielded tetramethyl-1,3,2-dioxaborolane scaffold, delivering enhanced stability and reactivity in cross-coupling transformations under standard conditions.

Application

4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its naphthalene moiety provides a rigid, electron-rich aryl handle that facilitates efficient coupling with a broad range of halides and pseudohalides. The tetramethyl substitution enhances stability and solubility, enabling straightforward purification and reliable performance in multistep syntheses of functionalized biaryls and complex heterocyclic scaffolds.

Synthesis

  • Route1
    • In-stock
      2-Iodonaphthalene|CS-W005581
      612-55-5
    • null|null
      25015-63-8
    • ~89%
    • In-stock
      4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane|CS-0041414
      256652-04-7

    References

    • Journal of Organometallic Chemistry, , vol. 640, # 1-2 p. 197 - 199
  • Route2
    • In-stock
      2-Bromonaphthalene|CS-W007537
      580-13-2
    • null|null
      61676-62-8
    • ~95%
    • In-stock
      4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane|CS-0041414
      256652-04-7

    References

    • Chemistry - A European Journal, , vol. 15, # 47 p. 12978 - 12992
  • Route3
    • In-stock
      Naphthalen-2-yl trifluoromethanesulfonate|CS-0182185
      3857-83-8
    • null|null
      25015-63-8
    • ~74%
    • In-stock
      4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxaborolane|CS-0041414
      256652-04-7

    References

    • Journal of Organic Chemistry, , vol. 65, # 1 p. 164 - 168

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.139
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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