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CS-W001157 4
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5-Iodo-2-nitrophenol

  • CAS No. 27783-55-7

  • Cat. No. CS-W007032
  • Purity≥96%
  • MDL No.MFCD12923199

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

5-Iodo-2-nitrophenol|CS-W007032

Structure of 27783-55-7

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General Information

  • CAS No. 27783-55-7
  • Cat. No. CS-W007032
  • Purity ≥96%
  • MDL No. MFCD12923199
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄INO₃
  • Molecular Weight 265.01
  • Synonym(s) 3-iodo-6-nitrophenol
  • SMILES IC1=CC(O)=C([N+]([O-])=O)C=C1

Description

5-Iodo-2-nitrophenol delivers a reactive iodine handle paired with an electron-deficient nitro group, enabling efficient coupling in cross-coupling and functionalization workflows. This bench-stable phenolic derivative integrates readily into complex molecular architectures under standard conditions.

Application

5-Iodo-2-nitrophenol serves as a versatile building block in medicinal chemistry and materials science, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. Its iodine handle facilitates efficient Suzuki, Stille, and Negishi couplings, while the ortho-nitro group provides compatibility with selective reduction and electrophilic substitution. The compound exhibits bench stability and is amenable to standard purification techniques, making it well-suited for iterative synthesis of complex heterocycles and API intermediates.

Synthesis

  • Route1

    References

    • VAN ANDEL RESEARCH INSTITUTE Patent: WO2005/95347 A1, 2005 ; Location in patent: Page/Page column 41 ;
  • Route2
    • null|null
      636-98-6
    • ~63%
    • null|null
      100-02-7
    • In-stock
      5-Iodo-2-nitrophenol|CS-W007032
      27783-55-7

    References

    • Makosza, Mieczyslaw; Sienkiewicz, Krzysztof Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4199 - 4208
  • Route3

    References

    • Reid, Carolyn S.; Zhu, Xiaohua; Pandharkar, Trupti; Werbovetz, Karl A.; Farahat, Abdelbasset A.; Boykin, David W. Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 22 p. 6806 - 6810,5

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07,GHS09
Signal Word : Danger
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H317-H318-H410
Precautionary Statements : P261-P264-P270-P272-P273-P280-P302+P352-P330-P362+P364-P391-P501

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Computational Chemistry Data

  • TPSA   63.37
  • LogP   1.905
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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