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CS-W001157 4
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Methyl 4-(cyanoacetyl)benzoate

  • CAS No. 69316-08-1

  • Cat. No. CS-W008257
  • Purity≥98%
  • MDL No.MFCD00015378

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

Methyl 4-(cyanoacetyl)benzoate|CS-W008257

Structure of 69316-08-1

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General Information

  • CAS No. 69316-08-1
  • Cat. No. CS-W008257
  • Purity ≥98%
  • MDL No. MFCD00015378
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₉NO₃
  • Molecular Weight None
  • Synonym(s) p-(Cyanoacetyl)benzoic acid methyl ester
  • SMILES O=C(OC)C1=CC=C(C(CC#N)=O)C=C1

Description

Methyl 4-(cyanoacetyl)benzoate features a cyanoacetyl group conjugated to an aromatic ring, delivering high reactivity in heterocyclic synthesis. This bench-stable ester integrates readily into Michael addition cascades and serves as a key precursor for functionalized benzimidazoles and quinoline derivatives.

Application

Methyl 4-(cyanoacetyl)benzoate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted benzimidazoles and other heterocyclic scaffolds via condensation and cyclization protocols. The molecule combines a readily functionalized cyanoacetyl group with a methyl ester, offering orthogonal reactivity for sequential transformations. Its bench-stable nature and compatibility with standard reaction conditions facilitate purification and scale-up, making it a practical choice for medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      7377-26-6
    • null|null
      372-09-8
    • ~79%
    • In-stock
      Methyl 4-(cyanoacetyl)benzoate|CS-W008257
      69316-08-1

    References

    • Nowill, Randall W.; Patel, Trisha J.; Beasley, David L.; Alvarez, Jose A.; Jackson III, Elizah; Hizer, Todd J.; Ghiviriga, Ion; Mateer, Scott C.; Feske, Brent D. Tetrahedron Letters, 2011 , vol. 52, # 19 p. 2440 - 2442
  • Route2

    References

    • Park, Ahbyeol; Lee, Sunwoo Organic Letters, 2012 , vol. 14, # 4 p. 1118 - 1121
  • Route3

    References

    • Pyo, Ayoung; Park, Ahbyeol; Jung, Hyunmin; Lee, Sunwoo Synthesis (Germany), 2012 , vol. 44, # 18 p. 2885 - 2888

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   67.16
  • LogP   1.56958
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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