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CS-W001157 4
Total: USD 88.00

2-Amino-5-cyanopyridine

  • CAS No. 4214-73-7

  • Cat. No. CS-W009186
  • Purity≥97%
  • MDL No.MFCD00128902

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

2-Amino-5-cyanopyridine|CS-W009186

Structure of 4214-73-7

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General Information

  • CAS No. 4214-73-7
  • Cat. No. CS-W009186
  • Purity ≥97%
  • MDL No. MFCD00128902
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅N₃
  • Molecular Weight None
  • Synonym(s) 6-aminopyridine-3-carbonitrile
  • SMILES N#CC1=CC=C(N=C1)N

Description

2-Amino-5-cyanopyridine features a dual functionalization pattern with an amino group and a cyano moiety positioned ortho to each other on the pyridine ring. This arrangement enables efficient integration into heterocyclic architectures, particularly in medicinal chemistry scaffolds and transition metal-catalyzed coupling reactions. The molecule exhibits enhanced solubility and stability under standard conditions, facilitating its use in synthetic workflows.

Application

2-Amino-5-cyanopyridine serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyridine scaffolds via nucleophilic addition and coupling reactions. Its dual functionality—amine and nitrile groups—facilitates orthogonal transformations, including amidation, cyclization, and transition-metal-catalyzed cross-couplings. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for scalable medicinal chemistry campaigns and API intermediate development.

Synthesis

  • Route1
    • In-stock
      2-Amino-5-bromopyridine|CS-D1666
      1072-97-5
    • null|null
      143-33-9
    • ~84%
    • In-stock
      2-Amino-5-cyanopyridine|CS-W009186
      4214-73-7

    References

    • Zanon, Jacopo; Klapars, Artis; Buchwald, Stephen L. Journal of the American Chemical Society, 2003 , vol. 125, # 10 p. 2890 - 2891
  • Route2
    • In-stock
      2-Amino-5-bromopyridine|CS-D1666
      1072-97-5
    • null|null
      7440-66-6
    • ~%
    • In-stock
      2-Amino-5-cyanopyridine|CS-W009186
      4214-73-7

    References

    • Medivir AB Patent: US5849769 A1, 1998 ;
  • Route3
    • null|null
      557-21-1
    • In-stock
      2-Amino-5-bromopyridine|CS-D1666
      1072-97-5
    • ~90%
    • In-stock
      2-Amino-5-cyanopyridine|CS-W009186
      4214-73-7

    References

    • Srivastava, Rajiv R.; Collibee, Scott E. Tetrahedron Letters, 2004 , vol. 45, # 48 p. 8895 - 8897

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302-H312-H314-H332
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P304+P341-P305+P351+P338-P310-P312-P330-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   62.7
  • LogP   0.53548
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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