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CS-W001157 4
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2,3-Dihydroxybenzonitrile

  • CAS No. 67984-81-0

  • Cat. No. CS-W018729
  • Purity≥97%
  • MDL No.MFCD02261930

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

2,3-Dihydroxybenzonitrile|CS-W018729

Structure of 67984-81-0

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General Information

  • CAS No. 67984-81-0
  • Cat. No. CS-W018729
  • Purity ≥97%
  • MDL No. MFCD02261930
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅NO₂
  • Molecular Weight 135.12
  • Synonym(s) 3-Cyanocatechol
  • SMILES N#CC1=CC=CC(O)=C1O

Description

2,3-Dihydroxybenzonitrile features a phenolic backbone with adjacent hydroxyl groups and a nitrile substituent at the para position relative to one hydroxyl. This arrangement imparts enhanced solubility and reactivity in polar solvents, enabling efficient coupling reactions in synthetic routes. The molecule exhibits bench-stable behavior under standard conditions and serves as a key intermediate in the synthesis of bioactive heterocycles and functionalized aromatics.

Application

2,3-Dihydroxybenzonitrile serves as a versatile building block in synthetic organic chemistry, enabling access to functionalized aromatic scaffolds via palladium-catalyzed coupling reactions. Its ortho-dihydroxy and nitrile groups offer complementary reactivity for selective transformations, including derivatization of phenolic hydroxyls and cyanide functional group interconversions. The compound exhibits good bench stability and facilitates purification through crystallization or chromatography, supporting its use in medicinal chemistry and materials synthesis workflows.

Synthesis

  • Route1

    References

    • Bergeron, Raymond J.; Wiegand, Jan; McManis, James S.; Weimar, William R.; Park, Jeong-Hyun; Eiler-McManis, Eileen; Bergeron, Jennifer; Brittenham, Gary M. Journal of Medicinal Chemistry, 2005 , vol. 48, # 3 p. 821 - 831
  • Route2

    References

    • Jih, Ru Hwu; Fung, Fuh Wong European Journal of Organic Chemistry, 2006 , # 11 p. 2513 - 2516
  • Route3

    References

    • Takeuchi, Yasuo; Ozaki, Satoru; Satoh, Masahiro; Mimura, Ken-Ichiro; Hara, Sei-Ichi; Abe, Hitoshi; Nishioka, Hiromi; Harayama, Takashi Chemical and Pharmaceutical Bulletin, 2010 , vol. 58, # 11 p. 1552 - 1553

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   64.25
  • LogP   0.96948
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   0

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