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CS-W001157 4
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4-Hydroxy-2-methylbenzonitrile

  • CAS No. 14143-26-1

  • Cat. No. CS-W022191
  • Purity≥97%
  • MDL No.MFCD16997502

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

4-Hydroxy-2-methylbenzonitrile|CS-W022191

Structure of 14143-26-1

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General Information

  • CAS No. 14143-26-1
  • Cat. No. CS-W022191
  • Purity ≥97%
  • MDL No. MFCD16997502
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO
  • Molecular Weight 133.15
  • Synonym(s) 2-CYANO-5-HYDROXYTOLUENE
  • SMILES N#CC1=CC=C(O)C=C1C

Description

4-Hydroxy-2-methylbenzonitrile features a strategically positioned hydroxyl group and nitrile moiety on a methyl-substituted benzene ring, enabling selective functionalization in synthetic routes. This electron-deficient aromatic scaffold delivers enhanced reactivity in coupling processes and serves as a robust building block for bioactive molecule synthesis under standard conditions.

Application

4-Hydroxy-2-methylbenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct functionalization at the phenolic hydroxyl group. Its ortho-methyl and cyano substituents provide steric and electronic modulation for downstream transformations. The compound exhibits good bench stability and facilitates efficient coupling reactions, purification via recrystallization, and compatibility with standard protecting group strategies.

Synthesis

  • Route1

    References

    • Yestrepsky, Bryan D.; Kretz, Colin A.; Xu, Yuanxi; Holmes, Autumn; Sun, Hongmin; Ginsburg, David; Larsen, Scott D. Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 6 p. 1538 - 1544
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      4-Hydroxy-2-methylbenzonitrile|CS-W022191
      14143-26-1

    References

    • Marx, John N.; Zuerker, Joe; Hahn, Young-sook Paik Tetrahedron Letters, 1991 , vol. 32, # 17 p. 1921 - 1924
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    • In-stock
      4-Hydroxy-2-methylbenzonitrile|CS-W022191
      14143-26-1

    References

    • Beer et al. Journal of the Chemical Society, 1949 , p. 885,889

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   44.02
  • LogP   1.5723
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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