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CS-W001157 4
Total: USD 88.00

4-Bromo-2-naphthalenamine

  • CAS No. 74924-94-0

  • Cat. No. CS-0040520
  • Purity≥98%
  • MDL No.MFCD17012399

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

4-Bromo-2-naphthalenamine|CS-0040520

Structure of 74924-94-0

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General Information

  • CAS No. 74924-94-0
  • Cat. No. CS-0040520
  • Purity ≥98%
  • MDL No. MFCD17012399
  • 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-2-amine
  • SMILES NC1=CC(Br)=C2C=CC=CC2=C1

Description

4-Bromo-2-naphthalenamine features a bromine substituent at the 4-position and an amino group at the 2-position of the naphthalene core, creating a highly functionalized scaffold. This electron-rich aromatic system enables efficient coupling in cross-coupling reactions, particularly under palladium catalysis. The molecule exhibits good stability under standard conditions and serves as a key intermediate in the synthesis of advanced pharmaceuticals and functional materials.

Application

4-Bromo-2-naphthalenamine serves as a versatile building block in the synthesis of functionalized naphthalene derivatives. Its bromine and amino groups enable straightforward cross-coupling reactions and electrophilic substitutions, facilitating access to complex heterocyclic systems and pharmaceutical intermediates. The compound exhibits good bench stability and is readily purified by recrystallization or column chromatography, making it well-suited for iterative synthetic workflows in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 1-Bromo-3-nitronaphthalene|CS-0469750
      7499-65-2
    • ~80%
    • In-stock
      4-Bromo-2-naphthalenamine|CS-0040520
      74924-94-0

    References

    • Oh, Soo-Jin; Hwang, Seok Jin; Jung, Jonghoon; Yu, Kuai; Kim, Jeongyeon; Choi, Jung Yoon; Hartzell, H. Criss; Roh, Eun Joo; Justin Lee Molecular Pharmacology, 2013 , vol. 84, # 5 p. 726 - 735
  • Route2

    References

    • Hodgson; Elliott Journal of the Chemical Society, 1935 , p. 1850,1852
  • Route3
    • 1-Acetamido-4-bromonaphthalene|CS-0205881
      91394-66-0
    • ~%
    • In-stock
      4-Bromo-2-naphthalenamine|CS-0040520
      74924-94-0

    References

    • Bergmann,E.D.; Blum,J. Journal of Organic Chemistry, 1961 , vol. 26, p. 3214 - 3216

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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