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CS-W001157 4
Total: USD 88.00

4-Bromo-2-methoxyaniline

  • CAS No. 59557-91-4

  • Cat. No. CS-W009042
  • Purity≥96%
  • MDL No.MFCD01204266

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

4-Bromo-2-methoxyaniline|CS-W009042

Structure of 59557-91-4

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General Information

  • CAS No. 59557-91-4
  • Cat. No. CS-W009042
  • Purity ≥96%
  • MDL No. MFCD01204266
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈BrNO
  • Molecular Weight 202.05
  • Synonym(s) None
  • SMILES NC1=CC=C(Br)C=C1OC

Description

4-Bromo-2-methoxyaniline features a bromine substituent at the para position relative to the amino group and a methoxy group ortho to the amine, creating a uniquely activated aromatic system. This electron-rich scaffold enables direct coupling in palladium-catalyzed cross-coupling reactions and serves as a key intermediate in the synthesis of bioactive heterocycles and functional dyes.

Application

4-Bromo-2-methoxyaniline serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient construction of heterocyclic scaffolds via Pd-catalyzed coupling reactions. Its bromo group facilitates cross-coupling with boronic acids and amines, while the methoxy and amino functionalities provide orthogonal reactivity for further derivatization. The compound exhibits excellent bench stability and is readily purified by crystallization or chromatography, making it ideal for multi-step synthesis workflows.

Synthesis

  • Route1
    • null|null
      90-04-0
    • ~83%
    • In-stock
      4-Bromo-2-methoxyaniline|CS-W009042
      59557-91-4
    • 2,4-Dibromo-6-methoxyaniline|CS-0211249
      88149-47-7

    References

    • Tetrahedron, , vol. 67, # 32 p. 5798 - 5805
  • Route2
    • null|null
      90-04-0
    • ~99%
    • In-stock
      4-Bromo-2-methoxyaniline|CS-W009042
      59557-91-4

    References

    • Bagmanov Russian Journal of Applied Chemistry, 2009 , vol. 82, # 9 p. 1570 - 1576
  • Route3
    • null|null
      90-04-0
    • ~84%
    • In-stock
      4-Bromo-2-methoxyaniline|CS-W009042
      59557-91-4
    • 4,5-Dibromo-2-methoxyaniline|CS-1716822
      367521-06-0

    References

    • NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria, Gabriella; BERTRAND, Jay, Aaron; GNOCCHI, Paola; MOTTO, Ilaria; NESI, Marcella; PANZERI, Achille; VIANELLO, Paola Patent: WO2013/14039 A1, 2013 ; Location in patent: Page/Page column 43 ; WO 2013/014039 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H317-H411
Precautionary Statements : P261-P264-P270-P272-P273-P280-P302+P352-P330-P362+P364-P391-P501

Quality Control

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Computational Chemistry Data

  • TPSA   35.25
  • LogP   2.0399
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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