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CS-W001157 4
Total: USD 88.00

3-Amino-5-bromo-2-chloropyridine

  • CAS No. 588729-99-1

  • Cat. No. CS-D0976
  • Purity≥97%
  • MDL No.MFCD02682092

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

3-Amino-5-bromo-2-chloropyridine|CS-D0976

Structure of 588729-99-1

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General Information

  • CAS No. 588729-99-1
  • Cat. No. CS-D0976
  • Purity ≥97%
  • MDL No. MFCD02682092
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BrClN₂
  • Molecular Weight 207.46
  • Synonym(s) None
  • SMILES NC1=CC(Br)=CN=C1Cl

Description

3-Amino-5-bromo-2-chloropyridine features a tri-functional pyridine core enabling direct coupling in C–N and C–C bond formations. The amino group facilitates nucleophilic engagement, while bromo and chloro substituents support palladium-catalyzed cross-coupling. This electron-deficient scaffold delivers high reactivity under standard conditions.

Application

3-Amino-5-bromo-2-chloropyridine serves as a versatile building block in medicinal chemistry, enabling site-selective functionalization via cross-coupling and nucleophilic substitution reactions. The amino group facilitates derivatization, while the bromo and chloro substituents offer orthogonal reactivity for palladium-catalyzed coupling processes. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for multi-step synthesis of heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • SMITHKLINE BEECHAM CORPORATION Patent: WO2008/157191 A2, 2008 ; Location in patent: Page/Page column 75 ; WO 2008/157191 A2
  • Route2
    • 2-Amino-5-bromo-N,N-dimethylpyridine-3-sulfonamide|CS-0930805
      1083326-15-1
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~88%
    • In-stock
      3-Amino-5-bromo-2-chloropyridine|CS-D0976
      588729-99-1

    References

    • CHAUDHARI, Amita; DHANAK, Dashyant; DONATELLI, Carla Ann; FAITG, Thomas H.; FENG, Yanhong; KNIGHT, Steven David; PARRISH, Cynthia A.; RALPH, Jeffrey M. Patent: US2008/293706 A1, 2008 ; Location in patent: Page/Page column 85 ; US 20080293706 A1
  • Route3

    References

    • Journal of Heterocyclic Chemistry, , vol. 40, # 2 p. 261 - 268

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   38.91
  • LogP   2.0797
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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