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CS-W001157 4
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1-Bromo-2-iodo-3-methylbenzene

  • CAS No. 869500-07-2

  • Cat. No. CS-W007210
  • Purity≥98%
  • MDL No.MFCD12547770

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

1-Bromo-2-iodo-3-methylbenzene|CS-W007210

Structure of 869500-07-2

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General Information

  • CAS No. 869500-07-2
  • Cat. No. CS-W007210
  • Purity ≥98%
  • MDL No. MFCD12547770
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrI
  • Molecular Weight 296.93
  • Synonym(s) 1-bromanyl-2-iodanyl-3-methyl-benzene
  • SMILES CC1=C(I)C(Br)=CC=C1

Description

1-Bromo-2-iodo-3-methylbenzene features a methyl group flanked by bromo and iodo substituents on a benzene ring, enabling precise functionalization in cross-coupling reactions. The ortho-halogen arrangement supports sequential metalation and palladium-catalyzed transformations, while the methyl group enhances solubility and stability under standard conditions.

Application

1-Bromo-2-iodo-3-methylbenzene serves as a versatile diaryl building block for palladium-catalyzed cross-coupling reactions. The orthogonal halogen reactivity enables sequential functionalization—bromine participates in Suzuki, Stille, or Negishi couplings, while the iodine moiety offers high reactivity in Buchwald–Hartwig amination or Sonogashira coupling. Bench-stable and readily purified by flash chromatography, it facilitates efficient access to substituted biaryl and heterocyclic scaffolds common in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Jancarik, Andrej; Rybacek, Jiri; Cocq, Kevin; Chocholousova, Jana Vacek; Vacek, Jaroslav; Pohl, Radek; Bednarova, Lucie; Fiedler, Pavel; Cisarova, Ivana; Stara, Irena G.; Stary, Ivo Angewandte Chemie - International Edition, 2013 , vol. 52, # 38 p. 9970 - 9975 Angew. Chem., 2013 , vol. 125, # 38 p. 10154 - 10159,6

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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