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CS-W001157 4
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2-Amino-6-bromobenzonitrile

  • CAS No. 77326-62-6

  • Cat. No. CS-W010573
  • Purity≥97%
  • MDL No.MFCD09834769

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

2-Amino-6-bromobenzonitrile|CS-W010573

Structure of 77326-62-6

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General Information

  • CAS No. 77326-62-6
  • Cat. No. CS-W010573
  • Purity ≥97%
  • MDL No. MFCD09834769
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂
  • Molecular Weight 197.04
  • Synonym(s) Bromo-6-amino-benzonitrile
  • SMILES N#CC1=C(Br)C=CC=C1N

Description

2-Amino-6-bromobenzonitrile features a bromine atom at the para position relative to the nitrile group, enabling facile cross-coupling reactions. The amino functionality provides a handle for derivatization, while the electron-withdrawing nitrile enhances reactivity in palladium-catalyzed transformations. This compound serves as a key intermediate in the synthesis of bioactive heterocycles and functionalized aromatic systems.

Application

2-Amino-6-bromobenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, quinolines, and other nitrogen-containing heterocycles via standard coupling and cyclization protocols. The molecule exhibits excellent bench stability, tolerates a range of reaction conditions, and facilitates straightforward purification due to its crystalline nature. Its dual functionality—amine and nitrile—supports orthogonal derivatization strategies, making it a reliable scaffold for targeted molecular design.

Synthesis

  • Route1
    • 2-Bromo-6-nitrobenzonitrile|CS-0186591
      79603-02-4
    • ~78%
    • In-stock
      2-Amino-6-bromobenzonitrile|CS-W010573
      77326-62-6

    References

    • Harris, Neil V.; Smith, Christopher; Bowden, Keith Journal of Medicinal Chemistry, 1990 , vol. 33, # 1 p. 434 - 444
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 24, # 6 p. 742 - 748
  • Route3
    • 2,6-Dinitrobenzonitrile|CS-0132605
      35213-00-4
    • ~%
    • In-stock
      2-Amino-6-bromobenzonitrile|CS-W010573
      77326-62-6

    References

    • Journal of Medicinal Chemistry, , vol. 33, # 1 p. 434 - 444

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

Quality Control

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Computational Chemistry Data

  • TPSA   49.81
  • LogP   1.90298
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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