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Methyl 5-amino-2-bromobenzoate

  • CAS No. 6942-37-6

  • Cat. No. CS-W005932
  • Purity≥95%
  • MDL No.MFCD00085568

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

Methyl 5-amino-2-bromobenzoate|CS-W005932

Structure of 6942-37-6

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General Information

  • CAS No. 6942-37-6
  • Cat. No. CS-W005932
  • Purity ≥95%
  • MDL No. MFCD00085568
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BrNO₂
  • Molecular Weight 230.06
  • Synonym(s) Benzoic acid, 5-amino-2-bromo-, methyl ester
  • SMILES O=C(OC)C1=CC(N)=CC=C1Br

Description

Methyl 5-amino-2-bromobenzoate features a bromine atom at the ortho position relative to the ester group and an amino substituent at the para position, creating a versatile scaffold for synthetic modifications. This electron-rich aromatic system enables efficient coupling reactions under mild conditions. The molecule exhibits enhanced solubility in common organic solvents and maintains stability during standard bench handling, facilitating its use in pharmaceutical intermediates and agrochemical synthesis.

Application

Methyl 5-amino-2-bromobenzoate serves as a versatile building block in medicinal chemistry, enabling sequential functionalization via the orthogonal reactivity of its amino and bromo groups. The amino group facilitates coupling reactions, while the bromo moiety supports palladium-catalyzed cross-couplings, allowing efficient access to substituted biaryls and complex heterocycles. Bench-stable and amenable to standard purification methods, it functions effectively in multi-step syntheses requiring precise regiocontrol.

Synthesis

  • Route1

    References

    • Chin, Elbert; Li, Jim; Lui, Albert Sui-Ting; Talamas, Francisco Xavier Patent: US2010/297073 A1, 2010 ; Location in patent: Page/Page column 20 ;
  • Route2
    • null|null
      67-56-1
    • 5-Acetamido-2-bromobenzoic acid|CS-0207294
      22921-67-1
    • ~%
    • In-stock
      Methyl 5-amino-2-bromobenzoate|CS-W005932
      6942-37-6

    References

    • WO2007/99200 A1, ; Page/Page column 9-10 ; WO 2007/099200 A1
  • Route3

    References

    • Synthesis, , # 8 art. no. P12608SS, p. 1305 - 1308

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   52.32
  • LogP   1.8179
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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