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CS-W001157 4
Total: USD 88.00

3-Amino-4-(trifluoromethyl)benzoic acid

  • CAS No. 125483-00-3

  • Cat. No. CS-W018904
  • Purity≥97%
  • MDL No.MFCD07784307

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

3-Amino-4-(trifluoromethyl)benzoic acid|CS-W018904

Structure of 125483-00-3

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General Information

  • CAS No. 125483-00-3
  • Cat. No. CS-W018904
  • Purity ≥97%
  • MDL No. MFCD07784307
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆F₃NO₂
  • Molecular Weight 205.13
  • Synonym(s) Benzoic acid, 3-amino-4-(trifluoromethyl)- (9CI)
  • SMILES NC1=C(C=CC(=C1)C(O)=O)C(F)(F)F

Description

3-Amino-4-(trifluoromethyl)benzoic acid features a strategically positioned trifluoromethyl group that enhances metabolic stability and lipophilicity, while the amino and carboxylic acid functionalities enable direct conjugation or salt formation. This scaffold integrates readily into bioactive molecules requiring electron-deficient aromatic cores and polar handles for solubility and derivatization under standard conditions.

Application

3-Amino-4-(trifluoromethyl)benzoic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its dual functionality—amine and carboxylic acid—facilitates efficient coupling reactions, including amide formation and cyclization pathways. The trifluoromethyl group enhances metabolic stability and lipophilicity, while the amino group provides a handle for derivatization under standard conditions. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step syntheses requiring orthogonal reactivity.

Synthesis

  • Route1

    References

    • Ameriks, Michael K.; Axe, Frank U.; Edwards, James P.; Grice, Cheryl A.; Cai, Hui; Gleason, Elizabeth Ann; Meduna, Steven P.; Tays, Kevin L.; Wiener, John J. M.; Wickboldt, Alvah T. Patent: US2008/200454 A1, 2008 ; Location in patent: Page/Page column 48 ; US 20080200454 A1
  • Route2

    References

    • Liebigs Annalen der Chemie, , # 6 p. 569 - 579

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   63.32
  • LogP   1.9858
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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