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CS-W001157 4
Total: USD 88.00

5-Bromo-6-chloronicotinic acid

  • CAS No. 29241-62-1

  • Cat. No. CS-W002863
  • Purity≥97%
  • MDL No.MFCD01927098

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

5-Bromo-6-chloronicotinic acid|CS-W002863

Structure of 29241-62-1

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General Information

  • CAS No. 29241-62-1
  • Cat. No. CS-W002863
  • Purity ≥97%
  • MDL No. MFCD01927098
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃BrClNO₂
  • Molecular Weight 236.45
  • Synonym(s) None
  • SMILES BrC(C=C(C(O)=O)C=N1)=C1Cl

Description

5-Bromo-6-chloronicotinic acid is a halogenated nicotinic acid derivative featuring bromine at the 5-position and chlorine at the 6-position of the pyridine ring. This electron-deficient heterocycle serves as a key building block in medicinal chemistry, enabling direct incorporation into bioactive molecules through coupling reactions. The dual halogenation enhances reactivity in cross-coupling processes, facilitating rapid diversification of pharmacophores.

Application

5-Bromo-6-chloronicotinic acid serves as a versatile building block for the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its ortho-halogenated pyridine core enables efficient palladium-catalyzed cross-coupling reactions, while the carboxylic acid group facilitates derivatization via amide or ester formation. The molecule exhibits good bench stability and is readily purified by recrystallization, making it well-suited for scalable synthetic applications in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2007/70818 A1, 2007 ; Location in patent: Page/Page column 103 ; WO 2007/070818 A1
  • Route2

    References

    • Andjelkovic, Mirjana; Benardeau, Agnes; Chaput, Evelyne; Hebeisen, Paul; Nettekoven, Matthias; Sander, Ulrike Obst; Panousis, Constantinos G.; Roever, Stephan Patent: US2008/85906 A1, 2008 ; Location in patent: Page/Page column 16 ;
  • Route3
    • 6-Hydroxynicotinic acid Avatrombopag Impurity|CS-0377520
      5006-66-6
    • ~%
    • In-stock
      5-Bromo-6-chloronicotinic acid|CS-W002863
      29241-62-1

    References

    • Roever, Stephan; Andjelkovic, Mirjana; Benardeau, Agnes; Chaput, Evelyne; Guba, Wolfgang; Hebeisen, Paul; Mohr, Susanne; Nettekoven, Matthias; Obst, Ulrike; Richter, Wolfgang F.; Ullmer, Christoph; Waldmeier, Pius; Wright, Matthew B. Journal of Medicinal Chemistry, 2013 , vol. 56, # 24 p. 9874 - 9896

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   50.19
  • LogP   2.1957
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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