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CS-W001157 4
Total: USD 88.00

3-Bromo-6-chloropyridine-2-carbonitrile

  • CAS No. 1053659-39-4

  • Cat. No. CS-0051455
  • Purity≥97%
  • MDL No.None

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

3-Bromo-6-chloropyridine-2-carbonitrile|CS-0051455

Structure of 1053659-39-4

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General Information

  • CAS No. 1053659-39-4
  • Cat. No. CS-0051455
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₂BrClN₂
  • Molecular Weight 217.45
  • Synonym(s) 3-Bromo-6-chloro-2-cyanopyridine
  • SMILES ClC1=CC=C(Br)C(=N1)C#N

Description

3-Bromo-6-chloropyridine-2-carbonitrile features a trifunctional pyridine core bearing bromo, chloro, and nitrile groups at strategic positions, enabling direct incorporation into cross-coupling and cyclization cascades. The electron-deficient aromatic ring facilitates nucleophilic substitution, while the carbonitrile group serves as a handle for derivatization. This compound exhibits bench-stable behavior under standard conditions and integrates efficiently into complex heterocyclic architectures.

Application

3-Bromo-6-chloropyridine-2-carbonitrile serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogenation pattern. The bromo group facilitates Suzuki, Stille, or Negishi coupling, while the chloro and nitrile functionalities offer additional sites for selective functionalization. Its bench-stable nature and compatibility with standard reaction conditions make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1
    • null|null
      889865-43-4
    • null|null
      7677-24-9
    • ~%
    • In-stock
      3-Bromo-6-chloropyridine-2-carbonitrile|CS-0051455
      1053659-39-4

    References

    • WO2009/111337 A1, ; Page/Page column 178-179 ; WO 2009/111337 A1
  • Route2
    • In-stock
      5-Bromo-2-chloropyridine|CS-W002767
      53939-30-3
    • null|null
      19158-51-1
    • ~67%
    • In-stock
      3-Bromo-6-chloropyridine-2-carbonitrile|CS-0051455
      1053659-39-4

    References

    • Organic Letters, , vol. 13, # 9 p. 2306 - 2309

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 : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   36.68
  • LogP   2.36918
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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