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CS-W001157 4
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4-Amino-2-bromobenzonitrile

  • CAS No. 53312-82-6

  • Cat. No. CS-W015684
  • Purity≥98%
  • MDL No.MFCD03695814

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

4-Amino-2-bromobenzonitrile|CS-W015684

Structure of 53312-82-6

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General Information

  • CAS No. 53312-82-6
  • Cat. No. CS-W015684
  • Purity ≥98%
  • MDL No. MFCD03695814
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂
  • Molecular Weight 197.04
  • Synonym(s) 2-Bromo-4-aminobenzonitrile
  • SMILES N#CC1=CC=C(N)C=C1Br

Description

4-Amino-2-bromobenzonitrile features a bromine atom at the ortho position relative to the nitrile group, enabling selective cross-coupling reactions. The amino functionality provides enhanced solubility and reactivity in transition metal-catalyzed processes. This electron-rich scaffold serves as a key building block for functionalized aromatic systems in medicinal chemistry and materials science.

Application

4-Amino-2-bromobenzonitrile serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal reactivity profile. The amino and bromo groups facilitate sequential functionalization, while the nitrile group offers compatibility with standard transformations. Its bench-stable nature and ease of purification support efficient synthesis of complex heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1
    • null|null
      1220099-39-7
    • ~85%
    • In-stock
      4-Amino-2-bromobenzonitrile|CS-W015684
      53312-82-6

    References

    • Mita, Yusuke; Dodo, Kosuke; Noguchi-Yachide, Tomomi; Hashimoto, Yuichi; Ishikawa, Minoru Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 4 p. 993 - 1005
  • Route2

    References

    • Huang, Kenneth He; Hughes, Philip; Ma, Wei; Ommen, Andy; Woodward, Angela; Veal, James; Barta, Thomas Patent: US2008/76813 A1, 2008 ; Location in patent: Page/Page column 26 ;
  • Route3

    References

    • Den Heeten, Rene; Van Der Boon, Leon J. P.; Broere, Daniel L. J.; Janssen, Elwin; De Kanter, Frans J. J.; Ruijter, Eelco; Orru, Romano V. A. European Journal of Organic Chemistry, 2012 , # 2 p. 275 - 280

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-H332-H335
Precautionary Statements : P264-P270-P330-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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