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CS-W001157 4
Total: USD 88.00

3,6-Diiodo-9H-carbazole

  • CAS No. 57103-02-3

  • Cat. No. CS-0040939
  • Purity≥95%
  • MDL No.MFCD00450017

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

3,6-Diiodo-9H-carbazole|CS-0040939

Structure of 57103-02-3

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General Information

  • CAS No. 57103-02-3
  • Cat. No. CS-0040939
  • Purity ≥95%
  • MDL No. MFCD00450017
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₇I₂N
  • Molecular Weight 419.00
  • Synonym(s) None
  • SMILES IC1=CC2=C(NC3=C2C=C(I)C=C3)C=C1

Description

3,6-Diiodo-9H-carbazole is a highly functionalized carbazole derivative featuring two iodine atoms at the 3 and 6 positions, enabling efficient coupling reactions in cross-coupling protocols. The electron-rich aromatic core supports robust π-conjugation, while the iodinated sites offer high reactivity in palladium-catalyzed transformations. This compound serves as a key building block for conjugated materials in organic electronics and synthetic intermediates in medicinal chemistry.

Application

3,6-Diiodo-9H-carbazole serves as a versatile building block for palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The iodine substituents offer high reactivity under standard Suzuki, Stille, and Negishi conditions, while the carbazole core provides inherent stability and π-conjugation valuable in materials and pharmaceutical synthesis. Its bench-stable solid form facilitates handling and purification in multi-step sequences.

Synthesis

  • Route1
    • null|null
      86-74-8
    • ~96%
    • In-stock
      3,6-Diiodo-9H-carbazole|CS-0040939
      57103-02-3

    References

    • Kumchoo, Trakool; Promarak, Vinich; Sudyoadsuk, Taweesak; Sukwattanasinitt, Mongkol; Rashatasakhon, Paitoon Chemistry - An Asian Journal, 2010 , vol. 5, # 10 p. 2162 - 2167
  • Route2
    • null|null
      86-74-8
    • ~8%
    • In-stock
      3-Iodo-9H-carbazole|CS-W021947
      16807-13-9
    • In-stock
      3,6-Diiodo-9H-carbazole|CS-0040939
      57103-02-3

    References

    • JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY; JAPAN SCIENCE AND TECHNOLOGY AGENCY Patent: US2011/34683 A1, 2011 ; Location in patent: Page/Page column 9; 10 ;
  • Route3
    • null|null
      86-74-8
    • ~9%
    • In-stock
      3,6-Diiodo-9H-carbazole|CS-0040939
      57103-02-3
    • null|null
      96853-45-1

    References

    • Bonesi; Erra-Balsells Journal of Heterocyclic Chemistry, 2001 , vol. 38, # 1 p. 77 - 87

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   15.79
  • LogP   4.5303
  • H_Acceptors   0
  • H_Donors   1
  • Rotatable_Bonds   0

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