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8-Bromonaphthalen-2-ol

  • CAS No. 7385-87-7

  • Cat. No. CS-0099484
  • Purity≥97%
  • MDL No.MFCD06656640

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

8-Bromonaphthalen-2-ol|CS-0099484

Structure of 7385-87-7

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General Information

  • CAS No. 7385-87-7
  • Cat. No. CS-0099484
  • Purity ≥97%
  • MDL No. MFCD06656640
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₇BrO
  • Molecular Weight 223.07
  • Synonym(s) 8-Bromo-2-naphthol
  • SMILES OC1=CC=C2C=CC=C(C2=C1)Br

Description

8-Bromonaphthalen-2-ol features a bromine atom at the 8-position of the naphthalene core, paired with a phenolic hydroxyl group at the 2-position. This arrangement imparts enhanced electrophilic reactivity and facilitates coupling reactions under mild conditions. The compound exhibits good stability under standard bench protocols and serves as a key intermediate in the synthesis of functionalized polycyclic systems.

Application

8-Bromonaphthalen-2-ol serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromide functionality. The phenolic hydroxyl group provides a handle for derivatization and enhances solubility, while the naphthalene core offers rigidity and extended π-conjugation. Its bench stability and compatibility with common protecting groups facilitate efficient synthesis of complex heterocycles and functionalized aromatic scaffolds.

Synthesis

  • Route1

    References

    • BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; SUN, Lihong; XIN, Zhili; ZHANG, Lei Patent: WO2014/25709 A1, 2014 ; Location in patent: Page/Page column 82 ;
  • Route2

    References

    • PFIZER INC. Patent: EP795328 A1, 1997 ; EP 0795328 A1
  • Route3
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    • In-stock
      8-Bromonaphthalen-2-ol|CS-0099484
      7385-87-7

    References

    • Iwamoto, Hajime; Yukimasa, Yoshiko; Fukazawa, Yoshimasa Tetrahedron Letters, 2002 , vol. 43, # 45 p. 8191 - 8194

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

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Computational Chemistry Data

  • TPSA   20.23
  • LogP   3.3079
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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