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

  • CAS No. 38197-43-2

  • Cat. No. CS-0137291
  • Purity≥97%
  • MDL No.MFCD14705101

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

2-Bromo-1-methoxy-3-methylbenzene|CS-0137291

Structure of 38197-43-2

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General Information

  • CAS No. 38197-43-2
  • Cat. No. CS-0137291
  • Purity ≥97%
  • MDL No. MFCD14705101
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉BrO
  • Molecular Weight 201.06
  • Synonym(s) 2-Bromo-3-methoxytoluene
  • SMILES CC1=C(Br)C(OC)=CC=C1

Description

This methoxy-substituted aryl bromide features a methyl group at the para position relative to the bromine, enabling efficient palladium-catalyzed cross-coupling reactions. The electron-donating methoxy and methyl groups enhance reactivity while maintaining stability under standard conditions.

Application

2-Bromo-1-methoxy-3-methylbenzene serves as a versatile aryl building block in cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. Its bromine functionality facilitates reliable Suzuki, Stille, and Negishi couplings under standard conditions, while the methoxy and methyl groups provide orthogonal directing effects and moderate electron-donating character. The compound exhibits good bench stability and is amenable to purification by silica gel chromatography, making it well-suited for iterative synthetic sequences in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Heescher, Carolin; Schollmeyer, Dieter; Nubbemeyer, Udo European Journal of Organic Chemistry, 2013 , # 20 p. 4399 - 4404
  • Route2
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    • In-stock
      2-Bromo-1-methoxy-3-methylbenzene|CS-0137291
      38197-43-2

    References

    • Fischer, Felix R.; Nuckolls, Colin Angewandte Chemie - International Edition, 2010 , vol. 49, # 40 p. 7257 - 7260
  • Route3

    References

    • Young, David C.; Vouros, Paul; Holick, Michael F.; Higuchi, Tetsuo Analytical Chemistry, 1992 , vol. 64, # 8 p. 837 - 842

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

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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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