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CS-W001157 4
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2-(Oxetan-3-ylidene)acetonitrile

  • CAS No. 1123787-67-6

  • Cat. No. CS-B0971
  • Purity≥98%
  • MDL No.MFCD14586415

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

2-(Oxetan-3-ylidene)acetonitrile|CS-B0971

Structure of 1123787-67-6

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General Information

  • CAS No. 1123787-67-6
  • Cat. No. CS-B0971
  • Purity ≥98%
  • MDL No. MFCD14586415
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅NO
  • Molecular Weight 95.10
  • Synonym(s) Oxetan-3-ylidene-acetonitrile
  • SMILES N#C/C=C1COC/1

Description

2-(Oxetan-3-ylidene)acetonitrile is a strained, electron-deficient heterocyclic building block featuring a reactive oxetane ring fused to an α,β-unsaturated nitrile. This combination enables rapid cycloaddition reactions and efficient integration into complex molecular architectures under mild conditions. The molecule's high ring strain and polarized double bond facilitate selective transformations in synthetic and medicinal chemistry applications.

Application

2-(Oxetan-3-ylidene)acetonitrile serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized oxetane scaffolds. Its α,β-unsaturated nitrile moiety facilitates conjugate additions and cycloaddition reactions, particularly with nucleophiles and dienes. The molecule exhibits bench stability and compatibility with common protecting groups, supporting straightforward purification and integration into multi-step syntheses. It functions effectively in the construction of heterocyclic systems relevant to medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; CHAND, Pooran; KOTIAN, Pravin, L.; KUMAR, V., Satish Patent: WO2010/14930 A2, 2010 ; Location in patent: Page/Page column 63 ; WO 2010/014930 A2
  • Route2
    • In-stock
      3-Oxetanone|CS-M1912
      6704-31-0
    • null|null
      16640-68-9
    • ~83%
    • In-stock
      2-(Oxetan-3-ylidene)acetonitrile|CS-B0971
      1123787-67-6

    References

    • Wuitschik, Georg; Carreira, Erick M.; Wagner, Bjoern; Fischer, Holger; Parrilla, Isabelle; Schuler, Franz; Rogers-Evans, Mark; Mueller, Klaus Journal of Medicinal Chemistry, 2010 , vol. 53, # 8 p. 3227 - 3246

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   33.02
  • LogP   0.46658
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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