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CS-W001157 4
Total: USD 88.00

3-Cyano-5-(trifluoromethyl)benzoic acid

  • CAS No. 942077-16-9

  • Cat. No. CS-0060191
  • Purity≥96%
  • MDL No.None

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

3-Cyano-5-(trifluoromethyl)benzoic acid|CS-0060191

Structure of 942077-16-9

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General Information

  • CAS No. 942077-16-9
  • Cat. No. CS-0060191
  • Purity ≥96%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₄F₃NO₂
  • Molecular Weight 215.13
  • Synonym(s) 3-cyano-5-trifluoromethylbenzoic acid
  • SMILES C1=C(C=C(C=C1C(=O)O)C(F)(F)F)C#N

Description

3-Cyano-5-(trifluoromethyl)benzoic acid features a trifluoromethyl group and a nitrile moiety positioned ortho to the carboxylic acid, creating a strongly electron-deficient aromatic core. This combination enhances its utility in coupling reactions and as a building block for bioactive molecules requiring high metabolic stability and precise electronic tuning.

Application

3-Cyano-5-(trifluoromethyl)benzoic acid serves as a versatile building block in medicinal chemistry and materials science, offering a robust combination of electron-withdrawing groups that enhance both metabolic stability and binding affinity. Its carboxylic acid functionality enables straightforward derivatization via esterification, amide coupling, or direct salt formation, while the cyano and trifluoromethyl groups provide excellent functional group tolerance and synthetic handle diversity. The molecule exhibits good bench stability and ease of purification, making it well-suited for scale-up and integration into complex synthetic sequences.

Synthesis

  • Route1
    • Methyl 3-cyano-5-(trifluoromethyl)benzoate|CS-0458870
      942077-15-8
    • ~98%
    • In-stock
      3-Cyano-5-(trifluoromethyl)benzoic acid|CS-0060191
      942077-16-9

    References

    • F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; DEHMLOW, Henrietta; ERICKSON, Shawn David; KARNACHI, Prabha Saba; KIM, Kyungjin; MARTIN, Rainerm, E.; MATTEI, Patrizio; OBST SANDER, Ulrike; PIETRANICO-COLE, Sherrie Lynn; RICHTER, Hans; ULLMER, Christoph Patent: WO2012/117000 A1, 2012 ; Location in patent: Page/Page column 197 ;
  • Route2
    • 3-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile|CS-0608761
      569370-38-3
    • ~84%
    • In-stock
      3-Cyano-5-(trifluoromethyl)benzoic acid|CS-0060191
      942077-16-9

    References

    • KOWA COMPANY, LTD. Patent: US2009/82352 A1, 2009 ; Location in patent: Page/Page column 28 ; US 20090082352 A1
  • Route3
    • null|null
      557-21-1
    • In-stock
      3-Bromo-5-(trifluoromethyl)benzoic acid|CS-W004826
      328-67-6
    • ~25%
    • In-stock
      3-Cyano-5-(trifluoromethyl)benzoic acid|CS-0060191
      942077-16-9

    References

    • BAYER INTELLECTUAL PROPERTY GMBH; SÜßMEIER, Frank; LOBELL, Mario; GRÜNEWALD, Sylvia; HÄRTER, Michael; BUCHMANN, Bernd; TELSER, Joachim; JÖRIßEN, Hannah; HEROULT, Melanie; KAHNERT, Antje; LUSTIG, Klemens; LINDNER, Niels Patent: US2013/190290 A1, 2013 ; Location in patent: Paragraph 0850; 0851; 0852; 0853 ;

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   61.09
  • LogP   2.27528
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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