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CS-W001157 4
Total: USD 88.00

2-Bromo-3-fluoroanisole

  • CAS No. 446-59-3

  • Cat. No. CS-W001103
  • Purity≥98%
  • MDL No.MFCD03788540

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

2-Bromo-3-fluoroanisole|CS-W001103

Structure of 446-59-3

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General Information

  • CAS No. 446-59-3
  • Cat. No. CS-W001103
  • Purity ≥98%
  • MDL No. MFCD03788540
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrFO
  • Molecular Weight 205.03
  • Synonym(s) 2-Bromo-3-fluorophenyl methyl ether
  • SMILES COC1=CC=CC(F)=C1Br

Description

2-Bromo-3-fluoroanisole features a strategically positioned bromo and fluoro substituent on an aromatic ring, enabling selective cross-coupling reactions. The methoxy group enhances solubility and directs regiochemistry, while the halogen combination offers orthogonal reactivity for sequential functionalization in synthetic sequences.

Application

2-Bromo-3-fluoroanisole serves as a versatile aryl halide building block for palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation in the synthesis of functionalized biaryls and heterocycles. The ortho-bromo and meta-fluoro substituents provide complementary reactivity for sequential functionalization, while the methoxy group enhances solubility and stabilizes intermediates. Bench-stable and compatible with standard reaction conditions, it facilitates streamlined access to complex molecular architectures in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Briner, Karin; Doecke, Christopher William; Mancuso, Vincent; Martinelli, Michael John; Richardson, Timothy Ivo; Rothhaar, Roger Ryan; Shi, Qing; Xie, Chaoyu Patent: US2004/82590 A1, 2004 ; Location in patent: Page/Page column 37 ; US 20040082590 A1
  • Route2

    References

    • Castellonese, Paul; Villa, Pierre Helvetica Chimica Acta, 1983 , vol. 66, # 4 p. 1068 - 1077
  • Route3

    References

    • Hodgson; Nixon Journal of the Chemical Society, 1931 , p. 981

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   2.5968
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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