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CS-W001157 4
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5-Iodo-2-methylphenol

  • CAS No. 183803-06-7

  • Cat. No. CS-0105564
  • Purity≥98%
  • MDL No.MFCD12923189

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

5-Iodo-2-methylphenol|CS-0105564

Structure of 183803-06-7

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General Information

  • CAS No. 183803-06-7
  • Cat. No. CS-0105564
  • Purity ≥98%
  • MDL No. MFCD12923189
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇IO
  • Molecular Weight 234.04
  • Synonym(s) 2-HYDROXY-4-IODOTOLUENE
  • SMILES OC1=CC(I)=CC=C1C

Description

5-Iodo-2-methylphenol features a strategically positioned iodine atom and methyl group on a phenolic scaffold, enabling direct functionalization in cross-coupling reactions. The electron-rich aromatic ring facilitates palladium-catalyzed transformations, while the hydroxyl group provides a handle for derivatization. This compound offers enhanced stability under standard conditions and serves as a key intermediate in medicinal chemistry and materials science applications.

Application

5-Iodo-2-methylphenol serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions such as Suzuki, Stille, and Negishi couplings. The iodide group offers high reactivity under mild conditions, while the ortho-methyl and phenolic hydroxyl functionalities provide steric and electronic modulation. Its bench-stable nature and compatibility with diverse functional groups facilitate efficient synthesis of complex heterocyclic scaffolds and bioactive molecules.

Synthesis

  • Route1
    • null|null
      2835-95-2
    • ~54%
    • In-stock
      5-Iodo-2-methylphenol|CS-0105564
      183803-06-7

    References

    • Chen, Yi; Luk, Kin-Chun; Rossman, Pamela Loreen; So, Sung-Sau Patent: US2008/9515 A1, 2008 ; Location in patent: Page/Page column 11-12 ;
  • Route2
    • null|null
      7664-93-9
    • null|null
      2835-95-2
    • ~%
    • In-stock
      5-Iodo-2-methylphenol|CS-0105564
      183803-06-7

    References

    • Hoechst Marion Roussel Patent: US5985853 A1, 1999 ;
  • Route3
    • null|null
      95-48-7
    • ~77%
    • In-stock
      5-Iodo-2-methylphenol|CS-0105564
      183803-06-7

    References

    • Shinde, Avinash T.; Zangade, Sainath B.; Chavan, Shivaji B.; Vibhute, Archana Y.; Nalwar, Yogesh S.; Vibhute, Yeshwant B. Synthetic Communications, 2010 , vol. 40, # 23 p. 3506 - 3513

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   20.23
  • LogP   2.30522
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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