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CS-W001157 4
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4-Amino-2-fluorobenzonitrile

  • CAS No. 53312-80-4

  • Cat. No. CS-W018702
  • Purity≥95%
  • MDL No.MFCD07368709

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

4-Amino-2-fluorobenzonitrile|CS-W018702

Structure of 53312-80-4

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General Information

  • CAS No. 53312-80-4
  • Cat. No. CS-W018702
  • Purity ≥95%
  • MDL No. MFCD07368709
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅FN₂
  • Molecular Weight 136.13
  • Synonym(s) 4-Cyano-3-fluoroaniline
  • SMILES C(#N)C1=C(C=C(N)C=C1)F

Description

4-Amino-2-fluorobenzonitrile features a strategically positioned amino group ortho to a fluorine substituent and para to a nitrile, enabling precise electronic modulation. This trifunctional scaffold integrates readily into diverse heterocyclic systems, serving as a key intermediate in the synthesis of pharmaceuticals and functional materials.

Application

4-Amino-2-fluorobenzonitrile serves as a versatile building block in medicinal chemistry, enabling the synthesis of fluorinated aromatic scaffolds via palladium-catalyzed cross-coupling and nucleophilic substitution reactions. Its ortho-fluoro and para-amino groups provide complementary reactivity for sequential functionalization, while the nitrile group supports downstream transformations including hydrolysis to carboxylic acids or reduction to primary amines. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for scalable synthesis applications.

Synthesis

  • Route1

    References

    • BRISTOL-MYERS SQUIBB COMPANY; WACKER, Dean, A.; ROSSI, Karen, A.; WANG, Ying; WU, Gang Patent: WO2010/9183 A1, 2010 ; Location in patent: Page/Page column 84 ; WO 2010/009183 A1
  • Route2
    • null|null
      1338209-74-7
    • ~92%
    • In-stock
      4-Amino-2-fluorobenzonitrile|CS-W018702
      53312-80-4

    References

    • Prakash, Anjanappa; Dibakar, Mullick; Selvakumar, Kumaravel; Ruckmani, Kandasamy; Sivakumar, Manickam Tetrahedron Letters, 2011 , vol. 52, # 43 p. 5625 - 5628
  • Route3

    References

    • Huang, Kenneth He; Hughes, Philip; Ma, Wei; Ommen, Andy; Woodward, Angela; Veal, James; Barta, Thomas Patent: US2008/76813 A1, 2008 ; Location in patent: Page/Page column 28 ;

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   1.27958
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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