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CS-W001157 4
Total: USD 88.00

1-Bromo-3-methoxy-5-methylbenzene

  • CAS No. 29578-83-4

  • Cat. No. CS-W007784
  • Purity≥98%
  • MDL No.None

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

1-Bromo-3-methoxy-5-methylbenzene|CS-W007784

Structure of 29578-83-4

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General Information

  • CAS No. 29578-83-4
  • Cat. No. CS-W007784
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉BrO
  • Molecular Weight 201.06
  • Synonym(s) benzene, 1-bromo-3-methoxy-5-methyl-; 1-Bromo-3-methoxy-5-methylbenzene
  • SMILES CC1=CC(OC)=CC(Br)=C1

Description

1-Bromo-3-methoxy-5-methylbenzene features a bromine atom flanked by electron-donating methoxy and methyl groups, enhancing reactivity in palladium-catalyzed cross-coupling. The ortho-substitution pattern promotes regioselective transformations while maintaining bench-stable handling properties under standard conditions.

Application

1-Bromo-3-methoxy-5-methylbenzene serves as a versatile aryl building block for palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl scaffolds. Its bromine functionality exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the methoxy and methyl groups provide orthogonal directing effects and enhanced solubility. The compound demonstrates excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • GILEAD SCIENCES, INC.; KOREAN RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY Patent: WO2009/5674 A2, 2009 ; Location in patent: Page/Page column 423 ;
  • Route2
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      3-Bromo-5-methylphenol|CS-W003584
      74204-00-5
    • null|null
      74-88-4
    • ~52%
    • In-stock
      1-Bromo-3-methoxy-5-methylbenzene|CS-W007784
      29578-83-4

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRENNEMAN, Jehrod Burnett; GINN, John; LOWE, Michael D.; SARKO, Christopher Ronald; TASBER, Edward S.; ZHANG, Zhonghua Patent: US2014/73629 A1, 2014 ; Location in patent: Paragraph 0297; 0313 ;
  • Route3
    • In-stock
      1,3-Dibromo-5-methoxybenzene|CS-W007953
      74137-36-3
    • null|null
      74-88-4
    • ~%
    • In-stock
      1-Bromo-3-methoxy-5-methylbenzene|CS-W007784
      29578-83-4

    References

    • WO2008/43567 A1, ; Page/Page column 32-33 ;

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   9.23
  • LogP   2.76612
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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