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CS-W001157 4
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Methyl 4-amino-3-(trifluoromethoxy)benzoate

  • CAS No. 457097-93-7

  • Cat. No. CS-0098155
  • Purity≥97%
  • MDL No.MFCD15527567

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

Methyl 4-amino-3-(trifluoromethoxy)benzoate|CS-0098155

Structure of 457097-93-7

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General Information

  • CAS No. 457097-93-7
  • Cat. No. CS-0098155
  • Purity ≥97%
  • MDL No. MFCD15527567
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈F₃NO₃
  • Molecular Weight None
  • Synonym(s) Benzoic acid, 4-amino-3-(trifluoromethoxy)-, methyl ester
  • SMILES O=C(OC)C1=CC=C(N)C(OC(F)(F)F)=C1

Description

Methyl 4-amino-3-(trifluoromethoxy)benzoate features a trifluoromethoxy group that enhances metabolic stability and lipophilicity, while the para-amino substituent enables direct coupling in peptide and pharmaceutical synthesis. This electron-rich aromatic scaffold integrates readily into bioactive scaffolds under standard conditions.

Application

Methyl 4-amino-3-(trifluoromethoxy)benzoate serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its trifluoromethoxy group enhances metabolic stability and membrane permeability, while the amino and ester functionalities offer orthogonal reactivity for coupling, acylation, and cyclization reactions. The compound exhibits good bench stability and is amenable to standard purification methods, facilitating efficient integration into multi-step synthetic sequences.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      4-Bromo-2-(trifluoromethoxy)aniline|CS-W002480
      175278-09-8
    • null|null
      201230-82-2
    • ~52%
    • In-stock
      Methyl 4-amino-3-(trifluoromethoxy)benzoate|CS-0098155
      457097-93-7

    References

    • BIOENERGENIX; MCCALL, John; KELLY, Robert, C.; ROMERO, Donna, L. Patent: WO2014/66795 A1, 2014 ; Location in patent: Paragraph 0175 ;
  • Route2
    • In-stock
      4-Amino-3-(trifluoromethoxy)benzoic acid|CS-W014741
      175278-22-5
    • null|null
      67-56-1
    • ~%
    • In-stock
      Methyl 4-amino-3-(trifluoromethoxy)benzoate|CS-0098155
      457097-93-7

    References

    • Daiichi Sankyo Company, Limited Patent: EP2017263 A1, 2009 ; Location in patent: Page/Page column 213 ; EP 2017263 A1
  • Route3

    References

    • THERAVANCE, INC. Patent: US2012/114600 A1, 2012 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   61.55
  • LogP   1.954
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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