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CS-W001157 4
Total: USD 88.00

1-Amino-4-bromonaphthalene

  • CAS No. 2298-07-9

  • Cat. No. CS-D1353
  • Purity≥98%
  • MDL No.MFCD00004023

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

1-Amino-4-bromonaphthalene|CS-D1353

Structure of 2298-07-9

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General Information

  • CAS No. 2298-07-9
  • Cat. No. CS-D1353
  • Purity ≥98%
  • MDL No. MFCD00004023
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈BrN
  • Molecular Weight 222.08
  • Synonym(s) 4-bromonaphthalen-1-amine
  • SMILES NC1=CC=C(Br)C2=C1C=CC=C2

Description

1-Amino-4-bromonaphthalene features a bromine atom at the para position relative to an amino group on a naphthalene core, enabling selective cross-coupling reactions. The electron-rich aromatic system enhances reactivity in palladium-catalyzed transformations, while the amino functionality offers direct handle for derivatization. This compound serves as a key intermediate in synthesizing functionalized polycyclic architectures and advanced organic materials.

Application

1-Amino-4-bromonaphthalene serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. The amino and bromo groups provide orthogonal reactivity for sequential functionalization, while the naphthalene core offers robust stability and compatibility with diverse reaction conditions. Its bench-stable solid form facilitates handling and purification, making it well-suited for the construction of complex heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1
    • null|null
      134-32-7
    • ~97%
    • In-stock
      1-Amino-4-bromonaphthalene|CS-D1353
      2298-07-9

    References

    • Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo Synthesis, 2004 , # 17 p. 2809 - 2812
  • Route2
    • null|null
      134-32-7
    • ~41%
    • In-stock
      1-Amino-4-bromonaphthalene|CS-D1353
      2298-07-9
    • In-stock
      2,4-Dibromonaphthalen-1-amine|CS-0112241
      20191-76-8

    References

    • Chretien, Jean-Mathieu; Zammattio, Francoise; Le Grognec, Erwan; Paris, Michael; Cahingt, Blanche; Montavon, Gilles; Quintard, Jean-Paul Journal of Organic Chemistry, 2005 , vol. 70, # 7 p. 2870 - 2873
  • Route3
    • 1-Acetamido-4-bromonaphthalene|CS-0205881
      91394-66-0
    • ~%
    • In-stock
      1-Amino-4-bromonaphthalene|CS-D1353
      2298-07-9

    References

    • Chemische Berichte, , vol. 4, p. 850

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   26.02
  • LogP   3.1845
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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