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CS-W001157 4
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5-Bromonaphthalen-1-amine

  • CAS No. 4766-33-0

  • Cat. No. CS-W005022
  • Purity≥98%
  • MDL No.MFCD07369883

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

5-Bromonaphthalen-1-amine|CS-W005022

Structure of 4766-33-0

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General Information

  • CAS No. 4766-33-0
  • Cat. No. CS-W005022
  • Purity ≥98%
  • MDL No. MFCD07369883
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈BrN
  • Molecular Weight 222.08
  • Synonym(s) 5-BROMO-NAPHTHALEN-1-YLAMINE
  • SMILES NC1=CC=CC2=C1C=CC=C2Br

Description

5-Bromonaphthalen-1-amine offers a strategic bromine handle at the 5-position of naphthalene, enabling efficient cross-coupling and functionalization. The primary amine group provides direct reactivity for conjugation, while the planar aromatic core ensures compatibility with transition-metal catalysis. This dual-functional architecture supports rapid access to complex polycyclic scaffolds in synthetic and medicinal chemistry workflows.

Application

5-Bromonaphthalen-1-amine serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. Its bromo group exhibits high reactivity under standard conditions, while the primary amine functions as a handle for derivatization or incorporation into heterocyclic frameworks. The compound demonstrates excellent bench stability and facilitates straightforward purification, making it well-suited for applications in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Wang, Binghe; Gao, Xingming; Yang, Wenqian; Fang, Hao; Yan, Yun Patent: US2007/274922 A1, 2007 ;
  • Route2
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    • In-stock
      5-Bromonaphthalen-1-amine|CS-W005022
      4766-33-0

    References

    • Tsuno,Y. et al. Bulletin of the Chemical Society of Japan, 1975 , vol. 48, p. 3356 - 3366
  • Route3

    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

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-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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