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4-Ethynylbenzoate sodium

  • CAS No. 144693-65-2

  • Cat. No. CS-0132435
  • Molecule weight168.12
  • Purity≥97%
  • MDL No.MFCD03426026

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

4-Ethynylbenzoate sodium |CS-0132435

Structure of 144693-65-2

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General Information

  • CAS No. 144693-65-2
  • Cat. No. CS-0132435
  • Purity ≥97%
  • MDL No. MFCD03426026
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅NaO₂
  • Molecular Weight 168.12
  • Synonym(s) None
  • SMILES O=C(O[Na])C1=CC=C(C#C)C=C1

Description

4-Ethynylbenzoate (sodium) delivers a robust, water-soluble platform for bioconjugation and click chemistry applications. This stable, bench-ready reagent features a terminal alkyne group paired with a carboxylate counterion, enabling efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC). The sodium salt enhances solubility in aqueous media without compromising reactivity, facilitating seamless integration into biological workflows.

Application

4-Ethynylbenzoate (sodium) serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated aryl-alkyne architectures. Its stability under ambient conditions and compatibility with palladium- and copper-based catalysis facilitate reliable Sonogashira and click-type transformations. The sodium salt enhances solubility in polar solvents, simplifying purification and reaction handling in synthetic workflows targeting functionalized arenes and heterocyclic scaffolds.

Synthesis

  • Route1

    References

    • Hale, Michael R.; Hill, Pamela; Lahiri, Sushmita; Miller, Matthew D.; Ross, Philip; Alm, Richard; Gao, Ning; Kutschke, Amy; Johnstone, Michele; Prince, Bryan; Thresher, Jason; Yang, Wei Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 8 p. 2362 - 2367
  • Route2

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 23, # 8 p. 2362 - 2367

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   0.9082
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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