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CS-W001157 4
Total: USD 88.00

3-Bromo-5-methylaniline

  • CAS No. 74586-53-1

  • Cat. No. CS-W016924
  • Purity≥97%
  • MDL No.MFCD11845553

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

3-Bromo-5-methylaniline|CS-W016924

Structure of 74586-53-1

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General Information

  • CAS No. 74586-53-1
  • Cat. No. CS-W016924
  • Purity ≥97%
  • MDL No. MFCD11845553
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈BrN
  • Molecular Weight 186.05
  • Synonym(s) None
  • SMILES C1=C(N)C=C(Br)C=C1C

Description

3-Bromo-5-methylaniline features a bromine atom at the meta position relative to the amino group and a methyl substituent at the para position, delivering enhanced electron density and steric profile. This configuration supports selective coupling reactions in pharmaceutical synthesis and enables efficient incorporation into complex heterocycles under standard conditions.

Application

3-Bromo-5-methylaniline serves as a valuable building block in medicinal chemistry and agrochemical synthesis, offering a regioselective platform for Suzuki-Miyaura and Buchwald-Hartwig coupling reactions. The bromo group enables efficient cross-coupling under mild conditions, while the ortho-methyl substituent provides steric and electronic modulation. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step syntheses of heterocyclic scaffolds and functionalized arylamines.

Synthesis

  • Route1

    References

    • Chemische Berichte, , vol. 13, p. 963 Chemische Berichte, , vol. 14, p. 417
  • Route2

    References

    • US5270309 A1, ; US 5270309 A
  • Route3
    • 2,3-Dibromo-5-methylaniline|CS-0462777
      96558-69-9
    • ~%
    • In-stock
      3-Bromo-5-methylaniline|CS-W016924
      74586-53-1

    References

    • Acta Chemica Scandinavica, , vol. 47, # 7 p. 701 - 705

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   26.02
  • LogP   2.33972
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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