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1-Bromo-2-nitronaphthalene

  • CAS No. 4185-55-1

  • Cat. No. CS-0161711
  • Purity≥98%
  • MDL No.MFCD00971807

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

1-Bromo-2-nitronaphthalene|CS-0161711

Structure of 4185-55-1

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General Information

  • CAS No. 4185-55-1
  • Cat. No. CS-0161711
  • Purity ≥98%
  • MDL No. MFCD00971807
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆BrNO₂
  • Molecular Weight 252.06
  • Synonym(s) 1-bromo-2-nitronaphthaL
  • SMILES O=[N+](C1=CC=C2C=CC=CC2=C1Br)[O-]

Description

1-Bromo-2-nitronaphthalene features a nitro group flanked by a bromine substituent on adjacent naphthalene rings, delivering enhanced reactivity in cross-coupling transformations. This electron-deficient scaffold enables efficient palladium-catalyzed coupling reactions under standard conditions, offering precise functionalization in synthetic organic chemistry workflows.

Application

1-Bromo-2-nitronaphthalene serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions and nucleophilic substitution processes. Its dual functionality—bromine for coupling and nitro group for reduction or further functionalization—facilitates the construction of complex polycyclic scaffolds. The compound exhibits good bench stability and is compatible with standard purification techniques, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 2-Nitronaphthalen-1-amine|CS-0524911
      607-23-8
    • ~%
    • In-stock
      1-Bromo-2-nitronaphthalene|CS-0161711
      4185-55-1

    References

    • Hodgson; Kilner Journal of the Chemical Society, 1926 , p. 8 Full Text Show Details Vesely; Chudozilov Bulletin de la Societe Chimique de France, 1925 , vol. <4> 37, p. 1441
  • Route2

    References

    • Hodgson; Kilner Journal of the Chemical Society, 1926 , p. 8
  • Route3
    • 8-Bromonaphthalene-1-sulfonic acid|CS-1154117
      63970-02-5
    • ~%
    • In-stock
      1-Bromo-2-nitronaphthalene|CS-0161711
      4185-55-1

    References

    • Lisitsyn,V.N.; Stankevich,G.S. Zhurnal Organicheskoi Khimii, 1977 , vol. 13, # 6 p. 1286 - 1289,1179 - 1182

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   3.5105
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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