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5-Amino-2-(trifluoromethyl)benzonitrile

  • CAS No. 354814-19-0

  • Cat. No. CS-0162563
  • Purity≥97%
  • MDL No.None

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

5-Amino-2-(trifluoromethyl)benzonitrile|CS-0162563

Structure of 354814-19-0

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General Information

  • CAS No. 354814-19-0
  • Cat. No. CS-0162563
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅F₃N₂
  • Molecular Weight 186.13
  • Synonym(s) 4-Phenoxy-pyridin-2-ylamine
  • SMILES N#CC1=CC(N)=CC=C1C(F)(F)F

Description

This trifluoromethyl-substituted benzonitrile features a strategically positioned amino group enabling direct functionalization in synthetic sequences. The electron-deficient aromatic ring enhances reactivity in transition-metal-catalyzed couplings, while the nitrile and amine moieties offer orthogonal handles for downstream derivatization. Bench-stable and moisture-tolerant, it integrates efficiently into complex molecular architectures.

Application

5-Amino-2-(trifluoromethyl)benzonitrile serves as a versatile building block in medicinal chemistry, enabling the synthesis of heterocyclic scaffolds via cyclization reactions. Its amino and nitrile groups offer orthogonal reactivity for downstream functionalization, while the trifluoromethyl group enhances metabolic stability and lipophilicity. The compound exhibits good bench stability and is amenable to standard purification techniques, facilitating integration into multi-step synthetic sequences.

Synthesis

  • Route1

    References

    • SMITHKLINE BEECHAM CORPORATION Patent: WO2009/58919 A1, 2009 ; Location in patent: Page/Page column 39 ; WO 2009/058919 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   49.81
  • LogP   2.15928
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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