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CS-W001157 4
Total: USD 88.00

1,8-Dibromonaphthalene

  • CAS No. 17135-74-9

  • Cat. No. CS-W002485
  • Molecule weight285.96
  • Purity≥96%
  • MDL No.MFCD00183574

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

1,8-Dibromonaphthalene|CS-W002485

Structure of 17135-74-9

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General Information

  • CAS No. 17135-74-9
  • Cat. No. CS-W002485
  • Purity ≥96%
  • MDL No. MFCD00183574
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆Br₂
  • Molecular Weight 285.96
  • Synonym(s) naphthalene, 1,8-dibromo-; 1,8-Dibromonaphthalene
  • SMILES Brc1cccc2c1c(Br)ccc2

Description

1,8-Dibromonaphthalene features two bromine atoms positioned at the peri-adjacent carbons of the naphthalene core, creating a sterically constrained, electron-deficient aromatic system. This configuration enhances its utility in transition-metal-catalyzed cross-coupling reactions, particularly in forming biaryl architectures with high regiocontrol. The compound exhibits bench-stable handling characteristics and integrates readily into synthetic sequences requiring orthogonal functionalization.

Application

1,8-Dibromonaphthalene serves as a versatile building block in organic synthesis, enabling efficient construction of polycyclic architectures through palladium-catalyzed cross-coupling reactions. Its orthogonal bromine positions facilitate sequential functionalization, while the naphthalene core provides inherent stability and planarity beneficial for materials and pharmaceutical intermediates. The compound exhibits excellent bench stability and simplifies purification due to low volatility and defined crystallinity, making it well-suited for scalable synthetic workflows.

Synthesis

  • Route1

    References

    • Chemical Communications, , vol. 48, # 67 p. 8434 - 8436
  • Route2
    • null|null
      506-68-3
    • null|null
      61767-59-7
    • ~34%
    • In-stock
      1,8-Dibromonaphthalene|CS-W002485
      17135-74-9

    References

    • Journal of Organic Chemistry, , vol. 55, # 4 p. 1311 - 1321
  • Route3

    References

    • Journal of Chemical Research, , vol. 35, # 12 p. 694 - 697

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H411
Precautionary Statements : P264-P270-P273-P330-P391-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   4.3648
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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