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4-Amino-2-hydroxybenzonitrile

  • CAS No. 67608-58-6

  • Cat. No. CS-0044060
  • Purity≥95%
  • MDL No.None

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

4-Amino-2-hydroxybenzonitrile|CS-0044060

Structure of 67608-58-6

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General Information

  • CAS No. 67608-58-6
  • Cat. No. CS-0044060
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆N₂O
  • Molecular Weight 134.14
  • Synonym(s) Benzonitrile, 4-amino-2-hydroxy-
  • SMILES N#CC1=CC=C(N)C=C1O

Description

4-Amino-2-hydroxybenzonitrile features a strategically positioned amino group and hydroxyl moiety flanking a nitrile functionality, enabling dual-directional conjugation in synthetic sequences. This ortho-substituted scaffold delivers enhanced solubility and reactivity under standard conditions, facilitating efficient incorporation into bioactive heterocycles and functional polymers.

Application

4-Amino-2-hydroxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling direct incorporation into heterocyclic scaffolds via cyclization or coupling reactions. Its ortho-hydroxyl and amino groups provide strong coordination for metal catalysis and facilitate downstream derivatization. The nitrile group offers high functional group tolerance and compatibility with standard transformations such as hydrolysis or nucleophilic addition. Bench-stable and readily purified by recrystallization, it functions efficiently in multi-step syntheses requiring regioselective reactivity.

Synthesis

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    References

    • Noel, Sabrina; Hoegy, Francoise; Rivault, Freddy; Rognan, Didier; Schalk, Isabelle J.; Mislin, Gaetan L.A. Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 1 p. 132 - 135
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    References

    • Ruiz-Caro, Juliana; Basavapathruni, Aravind; Kim, Joseph T.; Bailey, Christopher M.; Wang, Ligong; Anderson, Karen S.; Hamilton, Andrew D.; Jorgensen, William L. Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 3 p. 668 - 671
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    • In-stock
      4-Amino-2-hydroxybenzonitrile|CS-0044060
      67608-58-6

    References

    • Borsche Justus Liebigs Annalen der Chemie, 1912 , vol. 390, p. 23

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

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Computational Chemistry Data

  • TPSA   70.04
  • LogP   0.84608
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   0

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