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Methyl 3-amino-5-bromo-2-methylbenzoate

  • CAS No. 1000342-11-9

  • Cat. No. CS-M3309
  • Purity≥97%
  • MDL No.MFCD08690071

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

Methyl 3-amino-5-bromo-2-methylbenzoate|CS-M3309

Structure of 1000342-11-9

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General Information

  • CAS No. 1000342-11-9
  • Cat. No. CS-M3309
  • Purity ≥97%
  • MDL No. MFCD08690071
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀BrNO₂
  • Molecular Weight 244.09
  • Synonym(s) 3-Amino-5-bromo-2-methylbenzoic Acid Methyl Ester
  • SMILES O=C(OC)C1=CC(Br)=CC(N)=C1C

Description

Methyl 3-amino-5-bromo-2-methylbenzoate features a strategically positioned amino group flanked by bromo and methyl substituents, enabling selective functionalization in synthetic sequences. This electron-rich aromatic scaffold supports efficient coupling reactions and integrates readily into complex molecular architectures under standard conditions.

Application

Methyl 3-amino-5-bromo-2-methylbenzoate serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct functionalization at the amino and bromo positions. Its ortho-methyl group enhances regioselectivity in electrophilic substitutions, while the methyl ester facilitates downstream derivatization. The compound exhibits good bench stability, moderate solubility in common organic solvents, and compatibility with palladium-catalyzed cross-coupling reactions, making it well-suited for modular synthesis of complex aromatic scaffolds.

Synthesis

  • Route1

    References

    • EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William Patent: WO2012/118812 A2, 2012 ; Location in patent: Page/Page column 312 ; WO 2012/118812 A2
  • Route2

    References

    • WO2012/118812 A2, ; WO 2012/118812 A2
  • Route3

    References

    • US2012/264734 A1, ; US 20120264734 A1

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   52.32
  • LogP   2.12632
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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