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CS-W001157 4
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2,6-Dibromobenzonitrile

  • CAS No. 6575-12-8

  • Cat. No. CS-0097910
  • Purity≥98%
  • MDL No.None

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

2,6-Dibromobenzonitrile|CS-0097910

Structure of 6575-12-8

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General Information

  • CAS No. 6575-12-8
  • Cat. No. CS-0097910
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₃Br₂N
  • Molecular Weight 260.91
  • Synonym(s) 2,6-dibromo-benzonitrile
  • SMILES N#CC1=C(C=CC=C1Br)Br

Description

2,6-Dibromobenzonitrile features a nitrile group flanked by bromine substituents at the 2 and 6 positions, creating a highly electron-deficient aromatic core. This configuration enables direct functionalization in cross-coupling reactions, particularly under palladium catalysis. The compound exhibits excellent stability under standard conditions and serves as a robust building block for synthesizing advanced pharmaceutical intermediates and functionalized materials.

Application

2,6-Dibromobenzonitrile serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal reactivity profile. The nitrile group provides a handle for further functionalization, while the bromine substituents facilitate Suzuki, Stille, and Negishi couplings under standard conditions. Its bench-stable nature and compatibility with diverse reaction environments make it well-suited for constructing complex aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • In-stock
      2,6-Dibromoaniline|CS-W007411
      608-30-0
    • null|null
      544-92-3
    • ~38%
    • In-stock
      2,6-Dibromobenzonitrile|CS-0097910
      6575-12-8

    References

    • Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth Patent: US2008/171756 A1, 2008 ; Location in patent: Page/Page column 30 ;
  • Route2
    • null|null
      100-47-0
    • ~%
    • In-stock
      2,6-Dibromobenzonitrile|CS-0097910
      6575-12-8

    References

    • Eaton, Philip E.; Martin, Ronald M. Journal of Organic Chemistry, 1988 , vol. 53, # 12 p. 2728 - 2732
  • Route3

    References

    • Claus; Weil Justus Liebigs Annalen der Chemie, 1892 , vol. 269, p. 219 Full Text Show Details Meyer,V.; Sudborough Chemische Berichte, 1894 , vol. 27, p. 1584

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   23.79
  • LogP   3.08328
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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