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5-Amino-3-bromobenzonitrile

  • CAS No. 49674-16-0

  • Cat. No. CS-W018633
  • Purity≥95%
  • MDL No.MFCD11109874

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

5-Amino-3-bromobenzonitrile|CS-W018633

Structure of 49674-16-0

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General Information

  • CAS No. 49674-16-0
  • Cat. No. CS-W018633
  • Purity ≥95%
  • MDL No. MFCD11109874
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂
  • Molecular Weight 197.03
  • Synonym(s) 3-Bromo-5-cyanoaniline
  • SMILES NC1=CC(=CC(=C1)Br)C#N

Description

5-Amino-3-bromobenzonitrile features a bromine substituent at the meta position relative to the nitrile group, enabling selective coupling reactions. The amino functionality enhances solubility and reactivity in cross-coupling processes. This electron-rich scaffold serves as a key intermediate for pharmaceutical and agrochemical synthesis.

Application

5-Amino-3-bromobenzonitrile serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal functional groups. The amino and nitrile moieties provide sites for derivatization, while the bromine facilitates Suzuki, Stille, or Negishi couplings. 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

    • COMENTIS, INC.; PURDUE RESEARCH FOUNDATION Patent: WO2009/42694 A1, 2009 ; Location in patent: Page/Page column 111 ; WO 2009/042694 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302+H312+H332-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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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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