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CS-W001157 4
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5-Bromoanthranilonitrile

  • CAS No. 39263-32-6

  • Cat. No. CS-W015683
  • Purity≥95%
  • MDL No.MFCD00158946

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

5-Bromoanthranilonitrile|CS-W015683

Structure of 39263-32-6

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General Information

  • CAS No. 39263-32-6
  • Cat. No. CS-W015683
  • Purity ≥95%
  • MDL No. MFCD00158946
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂
  • Molecular Weight 197.03
  • Synonym(s) None
  • SMILES BrC1=CC=C(N)C(C#N)=C1

Description

5-Bromoanthranilonitrile features a brominated anthranilic acid scaffold with a nitrile group at the para position, enabling direct incorporation into heterocyclic systems. This electron-deficient aryl halide facilitates palladium-catalyzed cross-coupling reactions under standard conditions, offering efficient access to complex aromatic scaffolds in medicinal chemistry and materials synthesis.

Application

5-Bromoanthranilonitrile serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted quinazolines and other nitrogen-containing scaffolds via cyclization reactions. Its bromine and nitrile functionalities offer orthogonal reactivity for palladium-catalyzed cross-coupling and nucleophilic transformations, respectively. Bench-stable and readily purified by recrystallization, it facilitates scalable synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • ARROW THERAPEUTICS LIMITED Patent: WO2007/80401 A1, 2007 ; Location in patent: Page/Page column 26 ; WO 2007/080401 A1
  • Route2

    References

    • Krishna Mohan; Narender; Srinivasu; Kulkarni; Raghavan Synthetic Communications, 2004 , vol. 34, # 12 p. 2143 - 2152
  • Route3

    References

    • Roche, Didier; Prasad, Kapa; Repic, Oljan; Blacklock, Thomas J. Tetrahedron Letters, 2000 , vol. 41, # 13 p. 2083 - 2085

Safety Information

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GHS Pictogram : N/A
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Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   49.81
  • LogP   1.90298
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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