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CS-W001157 4
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2-Amino-5-(trifluoromethyl)benzonitrile

  • CAS No. 6526-08-5

  • Cat. No. CS-W019981
  • Molecule weight186.13
  • Purity≥97%
  • MDL No.MFCD03407465

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

2-Amino-5-(trifluoromethyl)benzonitrile|CS-W019981

Structure of 6526-08-5

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General Information

  • CAS No. 6526-08-5
  • Cat. No. CS-W019981
  • Purity ≥97%
  • MDL No. MFCD03407465
  • 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-Amino-3-cyanobenzotrifluoride, 2-Cyano-4-(trifluoromethyl)aniline
  • SMILES NC1=C(C#N)C=C(C(F)(F)F)C=C1

Description

2-Amino-5-(trifluoromethyl)benzonitrile features a trifluoromethyl group that imparts strong electron-withdrawing character and enhanced metabolic stability, while the amino and nitrile functionalities enable versatile coupling reactions. This compound serves as a key building block in medicinal chemistry for synthesizing bioactive heterocycles and functional materials under standard conditions.

Application

2-Amino-5-(trifluoromethyl)benzonitrile serves as a versatile building block in medicinal chemistry, enabling the synthesis of heterocyclic scaffolds through standard coupling and cyclization protocols. Its trifluoromethyl group enhances metabolic stability and lipophilicity, while the amino and nitrile functionalities provide orthogonal reactivity for downstream functionalization. The compound exhibits good bench stability and is amenable to purification via recrystallization or column chromatography, facilitating integration into multi-step syntheses.

Synthesis

  • Route1
    • null|null
      544-92-3
    • In-stock
      4-Amino-3-iodobenzotrifluoride|CS-W007562
      163444-17-5
    • ~%
    • In-stock
      2-Amino-5-(trifluoromethyl)benzonitrile|CS-W019981
      6526-08-5

    References

    • WO2007/41494 A2, ; Page/Page column 34 ;
  • Route2
    • null|null
      544-92-3
    • In-stock
      2-Bromo-4-(trifluoromethyl)aniline|CS-W004796
      57946-63-1
    • ~47%
    • In-stock
      2-Amino-5-(trifluoromethyl)benzonitrile|CS-W019981
      6526-08-5

    References

    • ELI LILLY AND COMPANY Patent: WO2004/14895 A1, 2004 ; Location in patent: Page 68 ; WO 2004/014895 A1
  • Route3
    • In-stock
      4-Amino-3-iodobenzotrifluoride|CS-W007562
      163444-17-5
    • null|null
      75-05-8
    • ~64%
    • In-stock
      2-Amino-5-(trifluoromethyl)benzonitrile|CS-W019981
      6526-08-5

    References

    • Song, Ren-Jie; Wu, Ji-Cheng; Liu, Yu; Deng, Guo-Bo; Wu, Cui-Yan; Wei, Wen-Ting; Li, Jin-Heng Synlett, 2012 , vol. 23, # 17 p. 2491 - 2496,6

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   49.81
  • LogP   2.15928
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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