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CS-W001157 4
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3-Bromo-2-hydroxybenzonitrile

  • CAS No. 13073-28-4

  • Cat. No. CS-0053980
  • Purity≥95%
  • MDL No.None

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

3-Bromo-2-hydroxybenzonitrile|CS-0053980

Structure of 13073-28-4

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General Information

  • CAS No. 13073-28-4
  • Cat. No. CS-0053980
  • Purity ≥95%
  • MDL No. None
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrNO
  • Molecular Weight 198.02
  • Synonym(s) 2-Bromo-6-cyanophenol
  • SMILES N#CC1=CC=CC(Br)=C1O

Description

3-Bromo-2-hydroxybenzonitrile features a bromine atom at the meta position relative to the hydroxyl group, creating a unique electronic profile ideal for cross-coupling reactions. The ortho-hydroxy and nitrile functionalities enable chelation and coordination in transition metal catalysis. This bench-stable derivative integrates readily into complex molecular architectures under standard conditions.

Application

3-Bromo-2-hydroxybenzonitrile serves as a versatile building block for the synthesis of functionalized heterocycles and bioactive intermediates. The bromo group enables palladium-catalyzed coupling reactions, while the ortho-hydroxyl and nitrile functionalities offer sites for derivatization, including cyclizations and metal coordination. Its bench-stable nature and compatibility with common protecting group strategies facilitate efficient synthetic planning in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • 2-(Benzyloxy)-3-bromobenzonitrile|CS-0673712
      862992-93-6
    • ~78%
    • In-stock
      3-Bromo-2-hydroxybenzonitrile|CS-0053980
      13073-28-4

    References

    • SMITHKLINE BEECHAM CORPORATION Patent: WO2005/77892 A1, 2005 ; Location in patent: Page/Page column 18 ;
  • Route2

    References

    • WO2009/158467 A2, ; Page/Page column 54 ;
  • Route3

    References

    • US2010/113512 A1, ; US 20100113512 A1

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   44.02
  • LogP   2.02638
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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