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CS-W001157 4
Total: USD 88.00

6-Hydroxynaphthalene-2-boronic acid

  • CAS No. 173194-95-1

  • Cat. No. CS-W000884
  • Molecule weightNone
  • Purity≥98%
  • MDL No.MFCD00092986

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

6-Hydroxynaphthalene-2-boronic acid|CS-W000884

Structure of 173194-95-1

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General Information

  • CAS No. 173194-95-1
  • Cat. No. CS-W000884
  • Purity ≥98%
  • MDL No. MFCD00092986
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₉BO₃
  • Molecular Weight None
  • Synonym(s) 6-Hydroxy-2-naphthylboronic Acid (contains varying amounts of Anhydride)
  • SMILES OC1=CC2=CC=C(B(O)O)C=C2C=C1

Description

6-Hydroxynaphthalene-2-boronic acid delivers a strategically positioned boronic acid group adjacent to a phenolic hydroxyl, enabling efficient coupling in Suzuki-Miyaura reactions. The hydroxyl enhances solubility and stabilizes the boronate moiety under physiological conditions. This dual-functional architecture supports robust cross-coupling with aryl halides and facilitates incorporation into bioactive scaffolds.

Application

6-Hydroxynaphthalene-2-boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl scaffolds. Its hydroxyl group provides orthogonal reactivity for selective functionalization, while the boronic acid moiety offers excellent stability and compatibility with diverse reaction conditions. Ideal for medicinal chemistry and materials synthesis, it facilitates straightforward purification and demonstrates broad functional group tolerance in standard coupling protocols.

Synthesis

  • Route1

    References

    • Idemitsu Kosan Co., Ltd.; ITO, Hirokatsu; KAWAMURA, Masahiro; KAWAMURA, Yuichiro; MIZUKI, Yumiko; SAITO, Hiroyuki Patent: EP2597094 A1, 2013 ; Location in patent: Paragraph 0093 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P305+P351+P338

Quality Control

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Computational Chemistry Data

  • TPSA   60.69
  • LogP   0.2252
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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