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CS-W001157 4
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1-Bromo-2-iodonaphthalene

  • CAS No. 90948-03-1

  • Cat. No. CS-0609093
  • Molecule weight332.96
  • Purity≥97%
  • MDL No.MFCD17012424

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

1-Bromo-2-iodonaphthalene|CS-0609093

Structure of 90948-03-1

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General Information

  • CAS No. 90948-03-1
  • Cat. No. CS-0609093
  • Purity ≥97%
  • MDL No. MFCD17012424
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆BrI
  • Molecular Weight 332.96
  • Synonym(s) 1-bromo-2-iodo-naphthalene
  • SMILES IC1=CC=C2C=CC=CC2=C1Br

Description

1-Bromo-2-iodonaphthalene features a naphthalene core with adjacent bromo and iodo substituents, enabling sequential cross-coupling reactions. This dual-halogenated scaffold supports precise functionalization in late-stage diversification, particularly in palladium-catalyzed coupling sequences. The ortho-halo arrangement facilitates controlled reactivity, where one halogen selectively engages under mild conditions while the other remains intact. This enables efficient access to complex biaryl architectures with tailored substitution patterns.

Application

1-Bromo-2-iodonaphthalene serves as a versatile biaryl building block in transition-metal-catalyzed cross-coupling reactions. The orthogonal reactivity of bromo and iodo groups enables sequential functionalization, facilitating the construction of complex naphthalene-based scaffolds. Its bench-stable nature and compatibility with palladium-catalyzed coupling protocols make it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
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    • In-stock
      1-Bromo-2-iodonaphthalene|CS-0609093
      90948-03-1

    References

    • Cottet, Fabrice; Castagnetti, Eva; Schlosser, Manfred Synthesis, 2005 , # 5 art. no. T11804SS, p. 798 - 803
  • Route2
    • 2-Acetonaphthone, ≥99%|CS-1268986
      93-08-3
    • ~%
    • In-stock
      1-Bromo-2-iodonaphthalene|CS-0609093
      90948-03-1

    References

    • Cottet, Fabrice; Castagnetti, Eva; Schlosser, Manfred Synthesis, 2005 , # 5 art. no. T11804SS, p. 798 - 803
  • Route3

    References

    • Meldola Journal of the Chemical Society, 1885 , vol. 47, p. 523 Journal of the Chemical Society, 1895 , vol. 67, p. 912

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
Precautionary Statements : P264-P280-P302+P352-P362+P364

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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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