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CS-W001157 4
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2-Amino-6-bromobenzoxazole

  • CAS No. 52112-66-0

  • Cat. No. CS-W006120
  • Purity≥95%
  • MDL No.MFCD01664214

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

2-Amino-6-bromobenzoxazole|CS-W006120

Structure of 52112-66-0

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General Information

  • CAS No. 52112-66-0
  • Cat. No. CS-W006120
  • Purity ≥95%
  • MDL No. MFCD01664214
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂O
  • Molecular Weight 213.03
  • Synonym(s) 2-benzoxazolamine, 6-bromo-
  • SMILES NC1=NC2=C(O1)C=C(Br)C=C2

Description

2-Amino-6-bromobenzoxazole is a heterocyclic aromatic compound featuring an amino group and a bromine atom at the 2- and 6-positions, respectively. This combination imparts enhanced reactivity for cross-coupling applications while maintaining stability under standard conditions. The electron-rich amine facilitates nucleophilic substitution, and the bromine serves as a reliable coupling handle in palladium-catalyzed transformations.

Application

2-Amino-6-bromobenzoxazole serves as a versatile building block in medicinal chemistry, enabling efficient access to heterocyclic scaffolds via palladium-catalyzed cross-coupling reactions. The bromo group facilitates reliable Suzuki, Stille, or Negishi coupling, while the amino functionality supports further derivatization through acylation or electrophilic substitution. Its bench-stable crystalline form and compatibility with standard synthetic workflows make it well-suited for iterative library synthesis and API development.

Synthesis

  • Route1

    References

    • Chikhale, Rupesh V.; Pant, Amit M.; Menghani, Sunil S.; Wadibhasme, Pankaj G.; Khedekar, Pramod B. South African Journal of Chemistry, 2013 , vol. 66, p. 254 - 262
  • Route2
    • Benzo[d]oxazol-2-amine Pramipexole Impurity|CS-0214018
      4570-41-6
    • ~62%
    • In-stock
      2-Amino-6-bromobenzoxazole|CS-W006120
      52112-66-0

    References

    • Stec, Markian M.; Andrews, Kristin L.; Booker, Shon K.; Caenepeel, Sean; Freeman, Daniel J.; Jiang, Jian; Liao, Hongyu; McCarter, John; Mullady, Erin L.; San Miguel, Tisha; Subramanian, Raju; Tamayo, Nuria; Wang, Ling; Yang, Kevin; Zalameda, Leeanne P.; Zhang, Nancy; Hughes, Paul E.; Norman, Mark H. Journal of Medicinal Chemistry, 2011 , vol. 54, # 14 p. 5174 - 5184
  • Route3
    • null|null
      1404480-07-4
    • ~%
    • In-stock
      2-Amino-6-bromobenzoxazole|CS-W006120
      52112-66-0

    References

    • INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward Patent: WO2010/51042 A1, 2010 ; Location in patent: Page/Page column 134 ;

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   52.05
  • LogP   2.1725
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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