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CS-W001157 4
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Methyl 3-ethynylbenzoate

  • CAS No. 10602-06-9

  • Cat. No. CS-W005738
  • Purity≥98%
  • MDL No.MFCD08703579

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

Methyl 3-ethynylbenzoate|CS-W005738

Structure of 10602-06-9

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General Information

  • CAS No. 10602-06-9
  • Cat. No. CS-W005738
  • Purity ≥98%
  • MDL No. MFCD08703579
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈O₂
  • Molecular Weight None
  • Synonym(s) Benzoic acid, 3-ethynyl-, methyl ester
  • SMILES O=C(OC)C1=CC=CC(C#C)=C1

Description

Methyl 3-ethynylbenzoate features a para-substituted aromatic ring with a terminal alkyne group, enabling efficient copper-catalyzed coupling reactions. This bench-stable reagent integrates readily into click chemistry workflows and serves as a key building block for conjugating bioactive molecules.

Application

Methyl 3-ethynylbenzoate serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to substituted biaryls and conjugated systems. Its terminal alkyne functionality exhibits excellent stability under standard bench conditions and demonstrates broad compatibility with Sonogashira, Glaser, and click chemistry protocols. The ester group provides orthogonal reactivity for downstream transformations, facilitating the synthesis of complex heterocycles and pharmaceutical intermediates.

Synthesis

  • Route1
    • Methyl 3-((trimethylsilyl)ethynyl)benzoate|CS-0253884
      77123-59-2
    • ~90%
    • In-stock
      Methyl 3-ethynylbenzoate|CS-W005738
      10602-06-9

    References

    • Gao, Mingshan; Duan, Lei; Luo, Jinfeng; Zhang, Lianwen; Lu, Xiaoyun; Zhang, Yan; Zhang, Zhang; Tu, Zhengchao; Xu, Yong; Ren, Xiaomei; Ding, Ke Journal of Medicinal Chemistry, 2013 , vol. 56, # 8 p. 3281 - 3295
  • Route2
    • null|null
      33577-97-8
    • ~72%
    • In-stock
      Methyl 3-ethynylbenzoate|CS-W005738
      10602-06-9

    References

    • Havens, Stephen J.; Hergenrother, Paul M. Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1763 - 1765
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 47, # 6 p. 1475 - 1486

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   26.3
  • LogP   1.4545
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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