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CS-W001157 4
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1-(5-Iodothiophen-2-yl)ethanone

  • CAS No. 30955-94-3

  • Cat. No. CS-W009466
  • Purity≥96%
  • MDL No.MFCD02093967

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

1-(5-Iodothiophen-2-yl)ethanone|CS-W009466

Structure of 30955-94-3

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General Information

  • CAS No. 30955-94-3
  • Cat. No. CS-W009466
  • Purity ≥96%
  • MDL No. MFCD02093967
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅IOS
  • Molecular Weight 252.08
  • Synonym(s) 2-Acetyl-5-iodothiophene
  • SMILES CC(=O)C1=CC=C(I)S1

Description

1-(5-Iodothiophen-2-yl)ethanone features a thiophene ring functionalized with an iodine atom at the 5-position and a ketone group at the 2-position, enabling direct coupling in cross-coupling reactions. The electron-deficient thiophene core enhances reactivity in palladium-catalyzed transformations, while the bench-stable ketone provides a handle for further derivatization.

Application

1-(5-Iodothiophen-2-yl)ethanone serves as a versatile building block for cross-coupling reactions, enabling efficient access to functionalized biaryl and heteroaryl architectures. Its iodine moiety facilitates palladium-catalyzed coupling with arylboranes, alkenylstannanes, and other nucleophiles under standard conditions. The ketone group provides additional synthetic handle for further transformations, including reduction or nucleophilic addition. Bench-stable and readily purified by crystallization, it supports scalable synthesis of pharmaceutical intermediates and advanced materials.

Synthesis

  • Route1

    References

    • D'Auria; Mauriello Tetrahedron Letters, 1995 , vol. 36, # 27 p. 4883 - 4884
  • Route2
    • Rivaroxaban impurity 4|CS-0166634
      6310-09-4
    • ~56%
    • In-stock
      1-(5-Iodothiophen-2-yl)ethanone|CS-W009466
      30955-94-3

    References

    • Adak, Laksmikanta; Yoshikai, Naohiko Journal of Organic Chemistry, 2011 , vol. 76, # 18 p. 7563 - 7568
  • Route3

    References

    • Synthesis, , # 3 p. 248 - 250

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06,GHS08
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H315-H319-H334-H335
Precautionary Statements : P261-P264-P271-P280-P284-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   2.5553
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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