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CS-W001157 4
Total: USD 88.00

2-Methoxy-6-methylbenzonitrile

  • CAS No. 53005-44-0

  • Cat. No. CS-W021712
  • Purity≥98%
  • MDL No.MFCD10699539

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

2-Methoxy-6-methylbenzonitrile|CS-W021712

Structure of 53005-44-0

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General Information

  • CAS No. 53005-44-0
  • Cat. No. CS-W021712
  • Purity ≥98%
  • MDL No. MFCD10699539
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉NO
  • Molecular Weight 147.17
  • Synonym(s) 2-Methoxy-6-methay benzonitrile
  • SMILES CC1=C(C#N)C(=CC=C1)OC

Description

2-Methoxy-6-methylbenzonitrile features a benzene ring bearing a methoxy group at the ortho position relative to the nitrile, paired with a methyl substituent at the para position. This electron-rich aromatic scaffold enables selective coupling in cross-coupling reactions and serves as a key building block in pharmaceutical synthesis due to its stability and tunable reactivity.

Application

2-Methoxy-6-methylbenzonitrile serves as a versatile building block in medicinal chemistry, enabling efficient access to substituted benzimidazoles and other heterocyclic scaffolds. Its ortho-directed reactivity facilitates electrophilic substitution and transition-metal-catalyzed coupling reactions. The nitrile group offers robust functional group tolerance and provides a handle for downstream transformations, including amide formation and reduction to primary amines. Bench-stable and readily purified by recrystallization or column chromatography, it is well-suited for scale-up and multi-step synthesis workflows.

Synthesis

  • Route1
    • null|null
      1030446-72-0
    • ~75%
    • In-stock
      2-Methoxy-6-methylbenzonitrile|CS-W021712
      53005-44-0

    References

    • Rhizen Pharmaceuticals SA Patent: US2012/289496 A1, 2012 ; Location in patent: Page/Page column 115 ;
  • Route2
    • 2-Methoxy-6-methylbenzamide|CS-0445961
      139583-90-7
    • ~89%
    • In-stock
      2-Methoxy-6-methylbenzonitrile|CS-W021712
      53005-44-0

    References

    • Fisher, Lawrence E.; Muchowski, Joseph M.; Clark, Robin D. Journal of Organic Chemistry, 1992 , vol. 57, # 9 p. 2700 - 2705
  • Route3
    • null|null
      67-56-1
    • null|null
      529-19-1
    • ~45%
    • In-stock
      2-Methoxy-6-methylbenzonitrile|CS-W021712
      53005-44-0

    References

    • Li, Wu; Sun, Peipei Journal of Organic Chemistry, 2012 , vol. 77, # 18 p. 8362 - 8366

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

Quality Control

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Computational Chemistry Data

  • TPSA   33.02
  • LogP   1.8753
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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