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CS-W001157 4
Total: USD 88.00

Methyl 2-cyanobenzoate

  • CAS No. 6587-24-2

  • Cat. No. CS-W005307
  • Purity≥96%
  • MDL No.MFCD00016376

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

Methyl 2-cyanobenzoate|CS-W005307

Structure of 6587-24-2

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General Information

  • CAS No. 6587-24-2
  • Cat. No. CS-W005307
  • Purity ≥96%
  • MDL No. MFCD00016376
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₂
  • Molecular Weight 161.16
  • Synonym(s) 2-(Methoxycarbonyl)benzonitrile
  • SMILES COC(=O)C1=C(C=CC=C1)C#N

Description

Methyl 2-cyanobenzoate features a strategically positioned cyano group ortho to the ester functionality, enabling unique electronic and steric effects in synthetic transformations. This configuration enhances reactivity in transition-metal-catalyzed couplings and facilitates selective functionalization in complex molecule assembly. The compound exhibits excellent stability under standard bench conditions and is compatible with a broad range of reaction environments.

Application

Methyl 2-cyanobenzoate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted benzimidazoles and other heterocyclic scaffolds via cyclization reactions. Its ortho-cyano and ester functionalities exhibit excellent compatibility with standard coupling and functional group interconversions, facilitating downstream derivatization. The compound demonstrates good bench stability and is readily purified by recrystallization or column chromatography, making it well-suited for use in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      681-84-5
    • In-stock
      2-Formylbenzonitrile|CS-W004147
      7468-67-9
    • ~80%
    • In-stock
      Methyl 2-cyanobenzoate|CS-W005307
      6587-24-2

    References

    • Lerebours, Rachel; Wolf, Christian Journal of the American Chemical Society, 2006 , vol. 128, # 40 p. 13052 - 13053
  • Route2

    References

    • Zheng, Kui; Liu, Bin; Chen, Shuyou; Chen, Fan Tetrahedron Letters, 2013 , vol. 54, # 38 p. 5250 - 5252
  • Route3
    • In-stock
      Benzoic acid, o-chloro-, methyl ester|CS-B1788
      610-96-8
    • null|null
      151-50-8
    • ~71%
    • In-stock
      Methyl 2-cyanobenzoate|CS-W005307
      6587-24-2

    References

    • Sundermeier, Mark; Zapf, Alexander; Mutyala, Sateesh; Baumann, Wolfgang; Sans, Juergen; Weiss, Stefan; Beller, Matthias Chemistry - A European Journal, 2003 , vol. 9, # 8 p. 1828 - 1836

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   50.09
  • LogP   1.34488
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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