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CS-W001157 4
Total: USD 88.00

2-(1H-Imidazol-4-yl)acetonitrile

  • CAS No. 18502-05-1

  • Cat. No. CS-0052326
  • Purity≥97%
  • MDL No.None

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

2-(1H-Imidazol-4-yl)acetonitrile|CS-0052326

Structure of 18502-05-1

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General Information

  • CAS No. 18502-05-1
  • Cat. No. CS-0052326
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅N₃
  • Molecular Weight 107.11
  • Synonym(s) 1H-Imidazole-5-acetonitrile
  • SMILES N#CCC1=CNC=N1

Description

2-(1H-Imidazol-4-yl)acetonitrile features a polar nitrile group flanked by a bioactive imidazole ring, enabling robust integration into pharmaceutical scaffolds. This bench-stable, moisture-tolerant building block facilitates efficient coupling in late-stage functionalization and transition-metal-catalyzed transformations.

Application

2-(1H-Imidazol-4-yl)acetonitrile serves as a versatile building block in medicinal chemistry, enabling efficient access to imidazole-containing scaffolds via standard functional group transformations. Its nitrile group facilitates nucleophilic additions and cyclizations, while the imidazole moiety provides hydrogen-bonding capacity and metabolic stability. The compound exhibits good bench stability and is compatible with common reaction conditions, making it a practical choice for synthesizing bioactive heterocycles and peptide extensions.

Synthesis

  • Route1
    • Histidine hydrochloride|CS-0368312
      6459-59-2
    • ~67%
    • In-stock
      2-(1H-Imidazol-4-yl)acetonitrile|CS-0052326
      18502-05-1

    References

    • Seley, Katherine L.; Salim, Samer; Zhang, Liang Organic Letters, 2005 , vol. 7, # 1 p. 63 - 66
  • Route2
    • null|null
      151-50-8
    • ~%
    • In-stock
      2-(1H-Imidazol-4-yl)acetonitrile|CS-0052326
      18502-05-1

    References

    • Journal of the Chemical Society, , vol. 99, p. 669,673 Journal of the Chemical Society, , vol. 109, p. 190,200
  • Route3

    References

    • Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, , vol. 26, # 8 p. 696 - 697

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301+H311+H331-H315-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   52.47
  • LogP   0.47578
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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