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CS-W001157 4
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1-Bromo-5-fluoronaphthalene

  • CAS No. 315-56-0

  • Cat. No. CS-0155711
  • Molecule weight225.06
  • Purity≥98%
  • MDL No.MFCD09258916

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

1-Bromo-5-fluoronaphthalene|CS-0155711

Structure of 315-56-0

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General Information

  • CAS No. 315-56-0
  • Cat. No. CS-0155711
  • Purity ≥98%
  • MDL No. MFCD09258916
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆BrF
  • Molecular Weight 225.06
  • Synonym(s) Naphthalene,1-bromo-5-fluoro
  • SMILES C1=CC2=C(C=CC=C2F)C(=C1)Br

Description

1-Bromo-5-fluoronaphthalene is a halogenated naphthalene derivative featuring complementary reactive sites for cross-coupling and electrophilic functionalization. The bromine at position 1 enables palladium-catalyzed coupling, while the fluorine at position 5 offers orthogonal reactivity or stabilization through inductive effects. This dual functionality supports precise molecular elaboration in synthetic organic chemistry.

Application

1-Bromo-5-fluoronaphthalene serves as a versatile building block in cross-coupling reactions, enabling efficient construction of biaryl scaffolds under palladium catalysis. The strategic placement of bromine and fluorine substituents provides orthogonal reactivity for sequential functionalization, while the naphthalene core offers enhanced stability and π-conjugation relevant to pharmaceutical and materials applications. Bench-stable and compatible with standard reaction conditions, it facilitates reliable synthesis of complex aromatic architectures.

Synthesis

  • Route1

    References

    • Repine, Joseph T.; Johnson, Douglas S.; White, Andrew D.; Favor, David A.; Stier, Michael A.; Yip, Judy; Rankin, Trent; Ding, Qizhu; Maiti, Samarendra N. Tetrahedron Letters, 2007 , vol. 48, # 31 p. 5539 - 5541
  • Route2
    • Tert-butyl (5-bromonaphthalen-1-yl)carbamate|CS-0753084
      846032-67-5
    • ~%
    • In-stock
      1-Bromo-5-fluoronaphthalene|CS-0155711
      315-56-0

    References

    • Tetrahedron Letters, , vol. 48, # 31 p. 5539 - 5541
  • Route3

    References

    • Tetrahedron Letters, , vol. 48, # 31 p. 5539 - 5541

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.7414
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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