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CS-W001157 4
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4-Iodo-1,2-dimethylbenzene

  • CAS No. 31599-61-8

  • Cat. No. CS-W016764
  • Purity≥98%
  • MDL No.MFCD00040989

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

4-Iodo-1,2-dimethylbenzene|CS-W016764

Structure of 31599-61-8

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General Information

  • CAS No. 31599-61-8
  • Cat. No. CS-W016764
  • Purity ≥98%
  • MDL No. MFCD00040989
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉I
  • Molecular Weight 232.06
  • Synonym(s) 4-pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-
  • SMILES CC1=CC(I)=CC=C1C

Description

4-Iodo-1,2-dimethylbenzene features a sterically hindered aryl iodide scaffold with methyl groups at ortho positions, enhancing stability and directing regioselective cross-coupling. This bench-stable reagent integrates efficiently into palladium-catalyzed transformations, enabling precise construction of complex substituted arenes under standard conditions.

Application

4-Iodo-1,2-dimethylbenzene serves as a versatile aryl iodide building block for palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation under standard Suzuki, Stille, and Negishi conditions. The ortho-methyl groups provide steric and electronic modulation, enhancing regioselectivity in subsequent transformations. Its bench-stable crystalline form facilitates handling and purification, making it well-suited for iterative synthesis of complex aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1
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      95-47-6
    • ~95%
    • In-stock
      4-Iodo-1,2-dimethylbenzene|CS-W016764
      31599-61-8

    References

    • Bailey, Lindsey; Handy, Scott T. Tetrahedron Letters, 2011 , vol. 52, # 18 p. 2413 - 2414
  • Route2
    • null|null
      95-47-6
    • ~%
    • In-stock
      4-Iodo-1,2-dimethylbenzene|CS-W016764
      31599-61-8
    • In-stock
      1-Iodo-2,3-dimethylbenzene|CS-W012941
      31599-60-7

    References

    • Tetrahedron Letters, , vol. 30, # 29 p. 3769 - 3772
  • Route3
    • null|null
      95-47-6
    • ~%
    • 1,2-Diiodo-4,5-dimethylbenzene|CS-0666562
      5182-67-2
    • In-stock
      4-Iodo-1,2-dimethylbenzene|CS-W016764
      31599-61-8

    References

    • Russian Journal of Organic Chemistry, , vol. 33, # 11 p. 1585 - 1597

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   0
  • LogP   2.90804
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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