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CS-W001157 4
Total: USD 88.00

4-Bromo-N-phenylaniline

  • CAS No. 54446-36-5

  • Cat. No. CS-W008122
  • Purity≥98%
  • MDL No.MFCD07779504

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

4-Bromo-N-phenylaniline|CS-W008122

Structure of 54446-36-5

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General Information

  • CAS No. 54446-36-5
  • Cat. No. CS-W008122
  • Purity ≥98%
  • MDL No. MFCD07779504
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₀BrN
  • Molecular Weight 248.12
  • Synonym(s) N-(4-Bromophenyl)aniline
  • SMILES BrC1=CC=C(C=C1)NC2=CC=CC=C2

Description

4-Bromo-N-phenylaniline integrates a bromine substituent at the para position of an aniline ring, paired with a direct N-phenyl linkage. This configuration delivers enhanced stability and predictable reactivity in cross-coupling transformations, enabling efficient construction of biaryl architectures under standard conditions.

Application

4-Bromo-N-phenylaniline serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. Its stability under standard reaction conditions, combined with predictable reactivity at the aryl bromide site, facilitates efficient synthesis of biaryl and heterocyclic scaffolds. The N-phenyl amine functionality provides a handle for further derivatization, while the molecule exhibits excellent bench stability and ease of purification.

Synthesis

  • Route1
    • In-stock
      Iodobenzene|CS-W008603
      591-50-4
    • null|null
      106-40-1
    • ~88%
    • In-stock
      4-Bromo-N-phenylaniline|CS-W008122
      54446-36-5

    References

    • WO2003/82777 A2, ; Page/Page column 43 ; WO 03/082777 A2
  • Route2
    • null|null
      122-39-4
    • ~94%
    • In-stock
      4-Bromo-N-phenylaniline|CS-W008122
      54446-36-5

    References

    • WO2009/72587 A1, ; Page/Page column 141-142 ;
  • Route3
    • null|null
      106-40-1
    • In-stock
      Phenylboronic acid|CS-W001090
      98-80-6
    • ~75%
    • In-stock
      4-Bromo-N-phenylaniline|CS-W008122
      54446-36-5

    References

    • Synthetic Communications, , vol. 34, # 12 p. 2177 - 2184

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07,GHS09
Signal Word : Danger
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335-H411
Precautionary Statements : P261-P264-P270-P271-P273-P280-P302+P352-P304+P340-P330-P362+P364-P391-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   12.03
  • LogP   4.1927
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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