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6-Chloro-2-(trifluoromethyl)pyridin-3-amine

  • CAS No. 117519-13-8

  • Cat. No. CS-0054544
  • Purity≥98%
  • MDL No.MFCD18261523

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

6-Chloro-2-(trifluoromethyl)pyridin-3-amine|CS-0054544

Structure of 117519-13-8

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General Information

  • CAS No. 117519-13-8
  • Cat. No. CS-0054544
  • Purity ≥98%
  • MDL No. MFCD18261523
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄ClF₃N₂
  • Molecular Weight 196.56
  • Synonym(s) None
  • SMILES NC1=CC=C(N=C1C(F)(F)F)Cl

Description

6-Chloro-2-(trifluoromethyl)pyridin-3-amine delivers a potent electron-deficient pyridine scaffold with orthogonal functional handles. The trifluoromethyl group enhances metabolic stability and lipophilicity, while the chloro substituent enables palladium-catalyzed coupling reactions. This molecule serves as a key building block in medicinal chemistry for targeted kinase inhibitors and bioactive heterocycles.

Application

6-Chloro-2-(trifluoromethyl)pyridin-3-amine serves as a versatile building block in medicinal chemistry, enabling efficient construction of heterocyclic scaffolds via palladium-catalyzed cross-coupling reactions. The chloro group facilitates C–C and C–N bond formation under standard conditions, while the trifluoromethyl and amine functionalities offer enhanced metabolic stability and hydrogen-bonding capacity. Bench-stable and compatible with common protecting groups, it supports scalable synthesis of kinase inhibitors and other bioactive molecules.

Synthesis

  • Route1

    References

    • Wiehn, Matthias S.; Vinogradova, Ekaterina V.; Togni, Antonio Journal of Fluorine Chemistry, 2010 , vol. 131, # 9 p. 951 - 957
  • Route2

    References

    • PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas Patent: WO2013/79223 A1, 2013 ;

Safety Information

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GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3259
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H318
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   38.91
  • LogP   2.336
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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