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5-Bromo-2-chloronicotinic acid methyl ester

  • CAS No. 78686-79-0

  • Cat. No. CS-D1791
  • Purity≥97%
  • MDL No.MFCD03844848

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

5-Bromo-2-chloronicotinic acid methyl ester|CS-D1791

Structure of 78686-79-0

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General Information

  • CAS No. 78686-79-0
  • Cat. No. CS-D1791
  • Purity ≥97%
  • MDL No. MFCD03844848
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrClNO₂
  • Molecular Weight 250.48
  • Synonym(s) Methyl 5-bromo-2-chloropyridine-3-carboxylate; 5-Bromo-2-chloronicotinic acid methyl ester
  • SMILES O=C(OC)C1=C(Cl)N=CC(Br)=C1

Description

5-Bromo-2-chloronicotinic acid methyl ester features a strategically positioned bromo and chloro substituent on the pyridine ring, enabling direct functionalization in cross-coupling reactions. The methyl ester group facilitates downstream derivatization while maintaining stability under standard conditions. This compound serves as a key building block for pharmaceutical intermediates and advanced materials synthesis.

Application

5-Bromo-2-chloronicotinic acid methyl ester serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The bromo group facilitates Suzuki, Stille, or Negishi couplings, while the chloro and ester functionalities offer complementary reactivity for sequential transformations. Bench-stable and readily purified by recrystallization, it functions efficiently in medicinal chemistry and agrochemical scaffold development.

Synthesis

  • Route1
    • null|null
      67-56-1
    • ~93%
    • In-stock
      5-Bromo-2-chloronicotinic acid methyl ester|CS-D1791
      78686-79-0

    References

    • Bristol-Myers Squibb Company Patent: US2007/78140 A1, 2007 ; Location in patent: Page/Page column 35 ; US 20070078140 A1
  • Route2
    • null|null
      67-56-1
    • In-stock
      5-Bromo-2-chloro-3-pyridinecarboxylic acid|CS-D1733
      29241-65-4
    • ~97%
    • In-stock
      5-Bromo-2-chloronicotinic acid methyl ester|CS-D1791
      78686-79-0

    References

    • Conn, P. Jeffrey; Lindsley, Craig W.; Stauffer, Shaun R.; Manka, Jason; Jacobs, Jon; Zhou, Ya; Bartolomé-Nebreda, José Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Jones, Carrie K. Patent: US2012/172391 A1, 2012 ; Location in patent: Page/Page column 79 ; US 20120172391 A1
  • Route3
    • In-stock
      5-Bromo-2-chloro-3-pyridinecarboxylic acid|CS-D1733
      29241-65-4
    • null|null
      18107-18-1
    • ~71%
    • In-stock
      5-Bromo-2-chloronicotinic acid methyl ester|CS-D1791
      78686-79-0

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENENATO, Kerry, Ellen; CHOY, Allison, Laura; HALE, Michael, Robin; HILL, Pamela; MARONE, Valerie; MILLER, Matthew Patent: WO2010/100475 A1, 2010 ; Location in patent: Page/Page column 87-88 ; WO 2010/100475 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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   39.19
  • LogP   2.2841
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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