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CS-W001157 4
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1-Bromo-8-iodonaphthalene

  • CAS No. 4044-58-0

  • Cat. No. CS-0094862
  • Purity≥98%
  • MDL No.MFCD11656276

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

1-Bromo-8-iodonaphthalene|CS-0094862

Structure of 4044-58-0

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General Information

  • CAS No. 4044-58-0
  • Cat. No. CS-0094862
  • Purity ≥98%
  • MDL No. MFCD11656276
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆BrI
  • Molecular Weight 332.96
  • Synonym(s) 8-Bromo-1-iodonaphthalene
  • SMILES IC1=C2C(C=CC=C2Br)=CC=C1

Description

1-Bromo-8-iodonaphthalene is a dihalogenated naphthalene derivative featuring complementary reactive halogens at opposite ends of the aromatic system. This strategic placement enables sequential cross-coupling reactions in synthetic sequences, facilitating efficient construction of complex biaryl architectures under palladium catalysis. The bromine and iodine substituents offer distinct reactivity profiles, allowing selective functionalization. This compound serves as a key building block for advanced organic materials and pharmaceutical intermediates.

Application

1-Bromo-8-iodonaphthalene serves as a versatile dihalogenated building block for transition-metal-catalyzed cross-coupling reactions. The orthogonal reactivity of bromine and iodine enables sequential functionalization, facilitating the construction of complex biaryl architectures. Its bench-stable nature and compatibility with palladium- and nickel-based catalysis make it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Cottet, Fabrice; Castagnetti, Eva; Schlosser, Manfred Synthesis, 2005 , # 5 art. no. T11804SS, p. 798 - 803
  • Route2

    References

    • Fieser; Seligman Journal of the American Chemical Society, 1939 , vol. 61, p. 136,140
  • Route3

    References

    • Fieser; Seligman Journal of the American Chemical Society, 1939 , vol. 61, p. 136,140

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-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   4.2069
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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