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CS-W001157 4
Total: USD 88.00

5-Bromo-2-cyanobenzeneacetonitrile

  • CAS No. 925672-88-4

  • Cat. No. CS-W019232
  • Purity≥96%
  • MDL No.MFCD09999213

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

5-Bromo-2-cyanobenzeneacetonitrile|CS-W019232

Structure of 925672-88-4

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General Information

  • CAS No. 925672-88-4
  • Cat. No. CS-W019232
  • Purity ≥96%
  • MDL No. MFCD09999213
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅BrN₂
  • Molecular Weight 221.05
  • Synonym(s) 4-bromo-2-(cyanomethyl)benzonitrile
  • SMILES BrC1=CC(=C(C=C1)C#N)CC#N

Description

5-Bromo-2-cyanobenzeneacetonitrile features a dual nitrile group flanking a brominated aromatic ring, enabling versatile coupling reactions. The electron-deficient aryl halide facilitates palladium-catalyzed cross-couplings, while the acetonitrile side chain offers a handle for further functionalization. This compound serves as a key intermediate in synthesizing bioactive heterocycles and advanced materials.

Application

5-Bromo-2-cyanobenzeneacetonitrile serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its dual electrophilic sites. The cyano group enhances reactivity in nucleophilic substitutions, while the bromine facilitates C–C bond formation under standard Suzuki or Stille conditions. Bench-stable and amenable to purification via flash chromatography, it functions effectively in the synthesis of substituted heterocycles and functionalized aryl scaffolds relevant to API development.

Synthesis

  • Route1

    References

    • Frohn, Mike; Buerli, Roland W.; Riahi, Bobby; Hungate, Randall W. Tetrahedron Letters, 2007 , vol. 48, # 3 p. 487 - 489
  • Route2
    • Methyl 2-(5-bromo-2-cyanophenyl)-2-cyanoacetate|CS-0678628
      925672-87-3
    • ~95%
    • In-stock
      5-Bromo-2-cyanobenzeneacetonitrile|CS-W019232
      925672-88-4

    References

    • Frohn, Mike; Buerli, Roland W.; Riahi, Bobby; Hungate, Randall W. Tetrahedron Letters, 2007 , vol. 48, # 3 p. 487 - 489
  • Route3

    References

    • Tetrahedron Letters, , vol. 48, # 3 p. 487 - 489

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302+H312-H315-H319-H331-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   47.58
  • LogP   2.38686
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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