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CS-W001157 4
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3-Bromo-5-nitrobenzonitrile

  • CAS No. 49674-15-9

  • Cat. No. CS-0060188
  • Purity≥97%
  • MDL No.MFCD00463804

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

3-Bromo-5-nitrobenzonitrile|CS-0060188

Structure of 49674-15-9

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General Information

  • CAS No. 49674-15-9
  • Cat. No. CS-0060188
  • Purity ≥97%
  • MDL No. MFCD00463804
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₃BrN₂O₂
  • Molecular Weight 227.01
  • Synonym(s) 1-Bromo-3-cyano-5-nitrobenzene
  • SMILES N#CC1=CC([N+]([O-])=O)=CC(Br)=C1

Description

3-Bromo-5-nitrobenzonitrile features a bromine atom and a nitro group flanking a nitrile-bearing benzene ring, enabling sequential functionalization in cross-coupling and nucleophilic substitution reactions. This electron-deficient scaffold integrates readily into complex molecular architectures under standard conditions.

Application

3-Bromo-5-nitrobenzonitrile serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its compatible bromo and nitrile functionalities. The nitro group enhances electrophilicity for nucleophilic substitution, while the molecule exhibits good bench stability and ease of purification, facilitating integration into multi-step syntheses of heterocyclic scaffolds and functionalized aromatic compounds.

Synthesis

  • Route1

    References

    • COMENTIS, INC.; PURDUE RESEARCH FOUNDATION Patent: WO2009/42694 A1, 2009 ; Location in patent: Page/Page column 71; 110-111 ; WO 2009/042694 A1
  • Route2
    • 3-Bromo-5-nitrobenzamide|CS-0192210
      54321-80-1
    • ~%
    • In-stock
      3-Bromo-5-nitrobenzonitrile|CS-0060188
      49674-15-9

    References

    • Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D. Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3243 - 3247
  • Route3
    • null|null
      51339-40-3
    • ~%
    • In-stock
      3-Bromo-5-nitrobenzonitrile|CS-0060188
      49674-15-9

    References

    • Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D. Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 11 p. 3243 - 3247

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   66.93
  • LogP   2.22898
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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