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CS-W001157 4
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Quinuclidine-4-carbonitrile

  • CAS No. 26458-78-6

  • Cat. No. CS-0044040
  • Purity≥97%
  • MDL No.MFCD00276610

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

Quinuclidine-4-carbonitrile|CS-0044040

Structure of 26458-78-6

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General Information

  • CAS No. 26458-78-6
  • Cat. No. CS-0044040
  • Purity ≥97%
  • MDL No. MFCD00276610
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₂N₂
  • Molecular Weight 136.19
  • Synonym(s) 1-Azabicyclo[2.2.2]octane-4-carbonitrile
  • SMILES N#CC12CCN(CC2)CC1

Description

Quinuclidine-4-carbonitrile is a sterically constrained, nitrogen-rich heterocycle featuring a pendant nitrile group. This configuration imparts enhanced nucleophilicity and favorable solubility in polar aprotic solvents. The molecule integrates readily into synthetic scaffolds requiring strong basicity with minimal steric interference.

Application

Quinuclidine-4-carbonitrile serves as a versatile bifunctional building block in medicinal chemistry, combining a rigid, sterically constrained quinuclidine scaffold with a reactive nitrile group. The nitrile enables downstream transformations such as amidation, reduction to primary amine, or conversion to imidazoles and other heterocycles. Its bench-stable nature and compatibility with diverse reaction conditions facilitate efficient synthesis of complex scaffolds.

Synthesis

  • Route1

    References

    • Svoboda, Jiri; Palecek, Jaroslav Collection of Czechoslovak Chemical Communications, 1995 , vol. 60, # 9 p. 1536 - 1540
  • Route2

    References

    • Kanai, Takeo; Nomoto, Seiichiro; Komatsu, Yuhki; Ogura,Katsuyuki Heterocycles, 1992 , vol. 34, # 11 p. 2137 - 2142
  • Route3

    References

    • Grob; Renk Helvetica Chimica Acta, 1954 , vol. 37, p. 1672,1676

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
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

  • TPSA   27.03
  • LogP   0.99588
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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