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CS-W001157 4
Total: USD 88.00

Ethyl 2-iodobenzoate

  • CAS No. 1829-28-3

  • Cat. No. CS-0085183
  • Purity≥98%
  • MDL No.MFCD00051796

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

Ethyl 2-iodobenzoate|CS-0085183

Structure of 1829-28-3

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General Information

  • CAS No. 1829-28-3
  • Cat. No. CS-0085183
  • Purity ≥98%
  • MDL No. MFCD00051796
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉IO₂
  • Molecular Weight 276.07
  • Synonym(s) 2-Iodobenzoic Acid Ethyl Ester
  • SMILES O=C(OCC)C1=CC=CC=C1I

Description

Ethyl 2-iodobenzoate delivers a reactive iodine handle ortho to an ester group, enabling direct functionalization in cross-coupling reactions. This bench-stable aryl iodide integrates readily into Suzuki, Stille, and Negishi transformations, offering predictable reactivity with minimal side processes. The ester moiety provides polarity for handling and purification.

Application

Ethyl 2-iodobenzoate serves as a versatile aryl iodide building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient C–C and C–heteroatom bond formation. Its ortho-iodine substitution facilitates selective functionalization under palladium or nickel catalysis, while the ester group provides compatibility with standard synthetic workflows. Bench-stable and readily purified by recrystallization, it functions reliably in Suzuki, Stille, and Negishi coupling protocols for the construction of biaryl and heterocyclic scaffolds.

Synthesis

  • Route1
    • null|null
      64-17-5
    • In-stock
      o-Iodobenzoic acid|CS-D0909
      88-67-5
    • ~90%
    • In-stock
      Ethyl 2-iodobenzoate|CS-0085183
      1829-28-3

    References

    • Hadjipavlou, Christiana; Kostakis, Ioannis K.; Pouli, Nicole; Marakos, Panagiotis; Pratsinis, Harris; Kletsas, Dimitris Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 18 p. 4822 - 4825
  • Route2
    • null|null
      64-17-5
    • In-stock
      2-Iodobenzoylchloride|CS-0156708
      609-67-6
    • ~87%
    • In-stock
      Ethyl 2-iodobenzoate|CS-0085183
      1829-28-3

    References

    • Zhdankin, Viktor V.; Koposov, Alexey Y.; Litvinov, Dmitry N.; Ferguson, Michael J.; McDonald, Robert; Luu, Thanh; Tykwinski, Rik R. Journal of Organic Chemistry, 2005 , vol. 70, # 16 p. 6484 - 6491
  • Route3
    • null|null
      74-96-4
    • null|null
      61717-82-6
    • ~87%
    • In-stock
      Ethyl 2-iodobenzoate|CS-0085183
      1829-28-3

    References

    • Zhang, Yuan; Han, Jianlei; Xu, Yanjun; Wei, Yuping Journal of Chemical Research, 2012 , vol. 36, # 5 p. 303 - 307

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   2.4679
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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