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CS-W001157 4
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4-Bromo-2-methoxybenzonitrile

  • CAS No. 330793-38-9

  • Cat. No. CS-W003329
  • Purity≥98%
  • MDL No.MFCD06738651

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

4-Bromo-2-methoxybenzonitrile|CS-W003329

Structure of 330793-38-9

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General Information

  • CAS No. 330793-38-9
  • Cat. No. CS-W003329
  • Purity ≥98%
  • MDL No. MFCD06738651
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrNO
  • Molecular Weight 212.04
  • Synonym(s) 4-BROMO-2-METHOXY-BENZONITRILE
  • SMILES COc1cc(Br)ccc1C#N

Description

4-Bromo-2-methoxybenzonitrile features a bromine atom at the para position relative to the nitrile group and a methoxy substituent at the ortho position, creating a sterically and electronically distinct aromatic scaffold. This combination enables selective coupling in transition-metal-catalyzed reactions, particularly Suzuki-Miyaura and Negishi transformations, due to enhanced reactivity at the brominated site. The electron-withdrawing nitrile group stabilizes adjacent intermediates while the methoxy moiety provides steric protection and solubility advantages under standard conditions.

Application

4-Bromo-2-methoxybenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromo and nitrile functionalities. The methoxy group enhances solubility and modulates electronic properties, while the nitrile provides a handle for downstream transformations. Its bench-stable nature and compatibility with standard reaction conditions facilitate efficient synthesis of complex heterocyclic scaffolds and functionalized aryl derivatives.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      4-Bromo-2-fluorobenzonitrile|CS-W007363
      105942-08-3
    • ~96%
    • In-stock
      4-Bromo-2-methoxybenzonitrile|CS-W003329
      330793-38-9

    References

    • BAYER HEALTHCARE AG Patent: WO2008/25509 A1, 2008 ; Location in patent: Page/Page column 91-92 ;
  • Route2
    • 4-Bromo-2-methoxybenzamide|CS-0119841
      812667-44-0
    • ~92%
    • In-stock
      4-Bromo-2-methoxybenzonitrile|CS-W003329
      330793-38-9

    References

    • DAIICHI SUNTORY PHARMA CO.,LTD.; DAIICHI SUNTORY BIOMEDICAL RESEARCH CO.,LTD. Patent: WO2004/111053 A1, 2004 ; Location in patent: Page/Page column 20-21 ; WO 2004/111053 A1
  • Route3

    References

    • BAYER PHARMACEUTICALS CORPORATION Patent: WO2003/72561 A1, 2003 ; Location in patent: Page/Page column 66-67 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P264-P270-P330-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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