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CS-W001157 4
Total: USD 88.00

6-Bromocinnoline

  • CAS No. 318276-72-1

  • Cat. No. CS-W022469
  • Purity≥95%
  • MDL No.MFCD09834644

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

6-Bromocinnoline|CS-W022469

Structure of 318276-72-1

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General Information

  • CAS No. 318276-72-1
  • Cat. No. CS-W022469
  • Purity ≥95%
  • MDL No. MFCD09834644
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrN₂
  • Molecular Weight 209.04
  • Synonym(s) Cinnoline,6-bromo
  • SMILES BrC1=CC2=CC=NN=C2C=C1

Description

6-Bromocinnoline features a bromine substituent at the 6-position of the cinnoline core, enabling direct functionalization in transition-metal-catalyzed coupling reactions. This electron-deficient heterocycle integrates readily into pharmaceutical and agrochemical scaffolds, offering enhanced reactivity in cross-coupling processes under standard conditions.

Application

6-Bromocinnoline serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions to construct biaryl and heteroaryl scaffolds. Its bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the cinnoline core offers inherent stability and compatibility with diverse functional groups. This compound facilitates efficient access to nitrogen-containing heterocycles relevant in medicinal chemistry and materials science, with excellent bench stability and straightforward purification.

Synthesis

  • Route1
    • null|null
      552330-88-8
    • ~24%
    • In-stock
      6-Bromocinnoline|CS-W022469
      318276-72-1

    References

    • Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L. Patent: US2003/199511 A1, 2003 ; Location in patent: Page/Page column 27 ;
  • Route2
    • null|null
      477909-64-1
    • ~96%
    • In-stock
      6-Bromocinnoline|CS-W022469
      318276-72-1

    References

    • Kimball, David B.; Weakley, Timothy J. R.; Haley, Michael M. Journal of Organic Chemistry, 2002 , vol. 67, # 18 p. 6395 - 6405
  • Route3
    • null|null
      1393462-55-9
    • ~66%
    • In-stock
      6-Bromocinnoline|CS-W022469
      318276-72-1

    References

    • Ball, Catherine J.; Gilmore, Jeremy; Willis, Michael C. Angewandte Chemie - International Edition, 2012 , vol. 51, # 23 p. 5718 - 5722

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   25.78
  • LogP   2.3923
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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