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CS-W001157 4
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2-Bromo-1-iodo-4-methylbenzene

  • CAS No. 71838-16-9

  • Cat. No. CS-W019589
  • Purity≥98%
  • MDL No.MFCD00079718

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

2-Bromo-1-iodo-4-methylbenzene|CS-W019589

Structure of 71838-16-9

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General Information

  • CAS No. 71838-16-9
  • Cat. No. CS-W019589
  • Purity ≥98%
  • MDL No. MFCD00079718
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrI
  • Molecular Weight 296.93
  • Synonym(s) 2-Bromo-4-methyliodobenzene; 2-Bromo-1-iodo-4-methylbenzene
  • SMILES CC1=CC=C(I)C(Br)=C1

Description

2-Bromo-1-iodo-4-methylbenzene features a dual halogenation pattern on a methyl-substituted benzene ring, enabling precise cross-coupling strategies. The bromo and iodo groups offer orthogonal reactivity, facilitating sequential functionalization in palladium-catalyzed transformations. This ortho-disubstituted scaffold provides excellent regiocontrol and stability under standard conditions.

Application

2-Bromo-1-iodo-4-methylbenzene serves as a versatile biaryl building block in cross-coupling chemistry, enabling palladium-catalyzed reactions such as Suzuki-Miyaura and Stille couplings. The orthogonal halogen reactivity—bromine typically undergoing coupling prior to iodine—facilitates sequential functionalization. Bench-stable and readily purified by column chromatography, it supports efficient synthesis of substituted arenes and complex scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5248 - 5252
  • Route2
    • null|null
      591-17-3
    • ~%
    • In-stock
      2-Bromo-1-iodo-4-methylbenzene|CS-W019589
      71838-16-9

    References

    • Journal of the Indian Chemical Society, , vol. 13, p. 187
  • Route3
    • null|null
      106-49-0
    • ~%
    • In-stock
      2-Bromo-1-iodo-4-methylbenzene|CS-W019589
      71838-16-9

    References

    • Tetrahedron Letters, , vol. 53, # 39 p. 5248 - 5252

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   3.36212
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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