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CS-W001157 4
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2-Amino-3-bromobenzonitrile; 3-Bromoanthranilonitrile

  • CAS No. 114344-60-4

  • Cat. No. CS-0028250
  • Purity≥97%
  • MDL No.None

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

2-Amino-3-bromobenzonitrile; 3-Bromoanthranilonitrile|CS-0028250

Structure of 114344-60-4

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General Information

  • CAS No. 114344-60-4
  • Cat. No. CS-0028250
  • Purity ≥97%
  • MDL No. None
  • 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-BroMoanthranilonitrile
  • SMILES N#CC1=C(C(Br)=CC=C1)N

Description

2-Amino-3-bromobenzonitrile features a bromine atom at the meta position relative to an amino group, delivering enhanced reactivity in cross-coupling processes. The nitrile functionality provides a polar handle for downstream transformations, while the electron-rich aromatic core supports efficient metal-catalyzed functionalization. This bench-stable compound integrates readily into complex molecular architectures.

Application

2-Amino-3-bromobenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal reactivity profile. The bromo group facilitates Suzuki, Stille, and Negishi couplings, while the amino and nitrile functionalities offer sites for further derivatization. Bench-stable and readily purified by recrystallization, it functions efficiently in multi-step syntheses of heterocyclic scaffolds and bioactive molecules.

Synthesis

  • Route1

    References

    • Synthetic Communications, , vol. 30, # 20 p. 3669 - 3675
  • Route2
    • null|null
      114344-59-1
    • ~12%
    • In-stock
      2-Amino-3-bromobenzonitrile; 3-Bromoanthranilonitrile|CS-0028250
      114344-60-4

    References

    • Campbell, James B.; Davenport, Timothy W. Synthetic Communications, 1989 , vol. 19, # 13-14 p. 2255 - 2264
  • Route3
    • null|null
      108-48-5
    • In-stock
      DBU|CS-0009461
      6674-22-2
    • null|null
      1025373-45-8
    • ~57%
    • In-stock
      2-Amino-3-bromobenzonitrile; 3-Bromoanthranilonitrile|CS-0028250
      114344-60-4

    References

    • ICI Americas Inc. Patent: US4975435 A1, 1990 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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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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