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CS-W001157 4
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4-Hydroxy-3-methylbenzonitrile

  • CAS No. 15777-70-5

  • Cat. No. CS-W006508
  • Molecule weight133.15
  • Purity≥97%
  • MDL No.MFCD11848762

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

4-Hydroxy-3-methylbenzonitrile|CS-W006508

Structure of 15777-70-5

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General Information

  • CAS No. 15777-70-5
  • Cat. No. CS-W006508
  • Purity ≥97%
  • MDL No. MFCD11848762
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO
  • Molecular Weight 133.15
  • Synonym(s) 2-methyl-4-cyanophenol
  • SMILES N#CC1=CC=C(O)C(C)=C1

Description

4-Hydroxy-3-methylbenzonitrile features a phenolic hydroxyl group and a nitrile functionality positioned ortho to each other on a methyl-substituted benzene ring. This arrangement enables dual reactivity, supporting coupling reactions and serving as a key scaffold in bioactive molecule synthesis. The compound exhibits enhanced solubility in organic solvents and stability under standard bench conditions.

Application

4-Hydroxy-3-methylbenzonitrile serves as a versatile building block in medicinal chemistry, enabling direct access to substituted phenolic scaffolds through standard coupling and functional group interconversion. Its ortho-hydroxynitrile motif provides compatibility with palladium-catalyzed cross-coupling, nucleophilic substitution, and electrophilic aromatic substitution reactions. The molecule exhibits bench stability, facilitates straightforward purification, and functions as a key intermediate in the synthesis of bioactive heterocycles and API precursors.

Synthesis

  • Route1

    References

    • Sergeev, Alexey G.; Schulz, Thomas; Torborg, Christian; Spannenberg, Anke; Neumann, Helfried; Beller, Matthias Angewandte Chemie, International Edition, 2009 , vol. 48, # 41 p. 7595 - 7599
  • Route2

    References

    • Pfizer Inc Patent: US2006/160786 A1, 2006 ; Location in patent: Page/Page column 36 ; US 20060160786 A1
  • Route3

    References

    • Sterling Winthrop Inc. Patent: US5464848 A1, 1995 ; US 5464848 A

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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