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CS-W001157 4
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3-Bromo-5-methoxybenzonitrile

  • CAS No. 867366-91-4

  • Cat. No. CS-W021871
  • Purity≥98%
  • MDL No.MFCD08061971

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

3-Bromo-5-methoxybenzonitrile|CS-W021871

Structure of 867366-91-4

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General Information

  • CAS No. 867366-91-4
  • Cat. No. CS-W021871
  • Purity ≥98%
  • MDL No. MFCD08061971
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrNO
  • Molecular Weight 212.04
  • Synonym(s) Benzonitrile,3-bromo-5-methoxy-
  • SMILES BrC1=CC(=CC(=C1)C#N)OC

Description

3-Bromo-5-methoxybenzonitrile features a bromine atom at the meta position relative to the nitrile group, paired with a methoxy substituent at the para position. This electron-rich aromatic scaffold enables direct functionalization in cross-coupling reactions and serves as a key intermediate in pharmaceutical synthesis.

Application

3-Bromo-5-methoxybenzonitrile serves as a versatile building block for the synthesis of biologically active heterocycles and pharmaceutical intermediates. Its bromo group enables palladium-catalyzed cross-coupling reactions, while the nitrile and methoxy functionalities offer orthogonal reactivity for further functionalization. The compound exhibits excellent bench stability and is readily purified by crystallization or column chromatography, making it well-suited for scalable synthetic workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • null|null
      867366-90-3
    • ~90%
    • In-stock
      3-Bromo-5-methoxybenzonitrile|CS-W021871
      867366-91-4

    References

    • Roche Palo Alto LLC Patent: US2008/45511 A1, 2008 ; Location in patent: Page/Page column 21 ;
  • Route2
    • null|null
      557-21-1
    • In-stock
      2-(3-Bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0173898
      401797-04-4
    • ~%
    • In-stock
      3-Bromo-5-methoxybenzonitrile|CS-W021871
      867366-91-4

    References

    • Liskey, Carl W.; Liao, Xuebin; Hartwig, John F. Journal of the American Chemical Society, 2010 , vol. 132, # 33 p. 11389 - 11391
  • Route3
    • null|null
      124-41-4
    • In-stock
      3-Bromo-5-fluorobenzonitrile|CS-D1719
      179898-34-1
    • ~%
    • In-stock
      3-Bromo-5-methoxybenzonitrile|CS-W021871
      867366-91-4

    References

    • WO2007/39736 A1, ; Page/Page column 65 ; WO 2007/039736 A1

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   33.02
  • LogP   2.32938
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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