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CS-W001157 4
Total: USD 88.00

4-Bromo-2,6-dimethylbenzonitrile

  • CAS No. 5757-66-4

  • Cat. No. CS-0153748
  • Purity≥97%
  • MDL No.MFCD01463960

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

4-Bromo-2,6-dimethylbenzonitrile|CS-0153748

Structure of 5757-66-4

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General Information

  • CAS No. 5757-66-4
  • Cat. No. CS-0153748
  • Purity ≥97%
  • MDL No. MFCD01463960
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈BrN
  • Molecular Weight 210.07
  • Synonym(s) 4-bromo-2,6-dimethylbenzenecarbonitrile
  • SMILES CC1=C(C#N)C(=CC(=C1)Br)C

Description

4-Bromo-2,6-dimethylbenzonitrile features a sterically hindered aromatic core with complementary electron-withdrawing nitrile and bromine substituents. This configuration enables selective cross-coupling reactions under mild conditions, while the methyl groups enhance solubility and stability in organic media.

Application

4-Bromo-2,6-dimethylbenzonitrile serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its stable nitrile group and ortho-methyl substitution pattern. The bromine functionality facilitates Suzuki, Stille, and Negishi couplings, while the electron-withdrawing nitrile enhances reactivity in nucleophilic aromatic substitution. Its bench-stable crystalline form simplifies handling and purification, making it ideal for multi-step synthesis of functionalized heterocycles and advanced API intermediates.

Synthesis

  • Route1
    • In-stock
      4-Bromo-2,6-dimethylaniline|CS-W019870
      24596-19-8
    • null|null
      544-92-3
    • ~68%
    • In-stock
      4-Bromo-2,6-dimethylbenzonitrile|CS-0153748
      5757-66-4

    References

    • Ferring B.V. Patent: EP1512687 A1, 2005 ; Location in patent: Page/Page column 8-9 ;
  • Route2
    • null|null
      88679-80-5
    • null|null
      143-33-9
    • ~91%
    • In-stock
      4-Bromo-2,6-dimethylbenzonitrile|CS-0153748
      5757-66-4

    References

    • ASTRAZENECA AB Patent: WO2008/130853 A1, 2008 ; Location in patent: Page/Page column 25-26 ; WO 2008/130853 A1
  • Route3
    • In-stock
      4-Bromo-2,6-dimethylaniline|CS-W019870
      24596-19-8
    • null|null
      544-92-3
    • null|null
      151-50-8
    • ~69%
    • In-stock
      4-Bromo-2,6-dimethylbenzonitrile|CS-0153748
      5757-66-4

    References

    • Ferring B.V. Patent: EP1449844 A1, 2004 ; Location in patent: Page 23 ; EP 1449844 A1

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   23.79
  • LogP   2.93762
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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