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CS-W001157 4
Total: USD 88.00

2-Bromo-3-methylaniline

  • CAS No. 54879-20-8

  • Cat. No. CS-W007900
  • Purity≥97%
  • MDL No.MFCD06411367

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

2-Bromo-3-methylaniline|CS-W007900

Structure of 54879-20-8

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General Information

  • CAS No. 54879-20-8
  • Cat. No. CS-W007900
  • Purity ≥97%
  • MDL No. MFCD06411367
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈BrN
  • Molecular Weight 186.05
  • Synonym(s) Benzenamine, 2-bromo-3-methyl-
  • SMILES NC1=CC=CC(C)=C1Br

Description

2-Bromo-3-methylaniline features a bromine atom at the ortho position relative to the amino group and a methyl substituent at the adjacent carbon, creating a sterically hindered, electron-rich aromatic system. This configuration enhances regioselectivity in coupling reactions and improves stability under standard bench conditions. The compound serves as a key building block for functionalized anilines in pharmaceutical synthesis and agrochemical development.

Application

2-Bromo-3-methylaniline serves as a valuable building block in medicinal chemistry and agrochemical synthesis, enabling direct functionalization at the aniline ring. Its ortho-bromo substituent facilitates palladium-catalyzed cross-coupling reactions, while the meta-methyl group enhances metabolic stability and modulates electronic properties. The compound exhibits good bench stability and is compatible with standard purification techniques, making it well-suited for multi-step synthesis workflows.

Synthesis

  • Route1

    References

    • ELI LILLY AND COMPANY Patent: WO2004/63155 A1, 2004 ; Location in patent: Page 120-121 ; WO 2004/063155 A1
  • Route2
    • null|null
      108-44-1
    • ~85%
    • In-stock
      2-Bromo-3-methylaniline|CS-W007900
      54879-20-8

    References

    • Ghiaci; Asghari Bulletin of the Chemical Society of Japan, 2001 , vol. 74, # 6 p. 1151 - 1152
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 53, # 6 p. 1170 - 1176

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-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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