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CS-W001157 4
Total: USD 88.00

2-Amino-5-(trifluoromethoxy)benzoic acid

  • CAS No. 83265-56-9

  • Cat. No. CS-W014744
  • Purity≥95%
  • MDL No.MFCD00176651

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

2-Amino-5-(trifluoromethoxy)benzoic acid|CS-W014744

Structure of 83265-56-9

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General Information

  • CAS No. 83265-56-9
  • Cat. No. CS-W014744
  • Purity ≥95%
  • MDL No. MFCD00176651
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆F₃NO₃
  • Molecular Weight 221.14
  • Synonym(s) 5-(Trifluoromethoxy)anthranilic acid
  • SMILES NC1=C(C=C(OC(F)(F)F)C=C1)C(O)=O

Description

2-Amino-5-(trifluoromethoxy)benzoic acid features a trifluoromethoxy group that imparts enhanced metabolic stability and lipophilicity, while the ortho-amino functionality enables direct coupling in peptide synthesis. This electron-deficient aromatic scaffold serves as a key building block for bioactive heterocycles and pharmaceutical intermediates under standard conditions.

Application

2-Amino-5-(trifluoromethoxy)benzoic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles and pharmaceutical scaffolds. Its ortho-amino and carboxylic acid functionalities offer orthogonal reactivity for coupling, amidation, and cyclization reactions. The trifluoromethoxy group enhances metabolic stability and lipophilicity, making it valuable for optimizing drug-like properties. Bench-stable and readily purified by recrystallization, it functions efficiently in standard peptide coupling and transition-metal-catalyzed transformations.

Synthesis

  • Route1
    • 2-Nitro-5-(trifluoromethoxy)benzoic acid|CS-0157042
      189359-65-7
    • ~97%
    • In-stock
      2-Amino-5-(trifluoromethoxy)benzoic acid|CS-W014744
      83265-56-9

    References

    • ASTRAZENECA AB Patent: WO2003/101956 A1, 2003 ; Location in patent: Page 47 ; WO 03/101956 A1
  • Route2
    • 2-((tert-Butoxycarbonyl)amino)-5-(trifluoromethoxy)benzoic acid|CS-0047013
      220107-35-7
    • ~93%
    • In-stock
      2-Amino-5-(trifluoromethoxy)benzoic acid|CS-W014744
      83265-56-9

    References

    • Leroux, Frederic; Castagnetti, Eva; Schlosser, Manfred Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4693 - 4699
  • Route3

    References

    • US6034256 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

Quality Control

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Computational Chemistry Data

  • TPSA   72.55
  • LogP   1.8656
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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