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CS-W001157 4
Total: USD 88.00

Fumaronitrile

  • CAS No. 764-42-1

  • Cat. No. CS-0022396
  • Purity≥98%
  • MDL No.MFCD00001928

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

Fumaronitrile|CS-0022396

Structure of 764-42-1

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General Information

  • CAS No. 764-42-1
  • Cat. No. CS-0022396
  • Purity ≥98%
  • MDL No. MFCD00001928
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₂N₂
  • Molecular Weight 78.07
  • Synonym(s) trans-Dicyanoethylene
  • SMILES N#C/C=C/C#N

Description

Fumaronitrile features a rigid, planar trans-dicyanoethylene structure that imparts high electron-withdrawing character. This configuration enables efficient participation in Diels-Alder reactions and conjugate additions, serving as a valuable dienophile and synthetic handle in heterocyclic construction under mild conditions.

Application

Fumaronitrile serves as a versatile dienophile in Diels–Alder reactions and a key building block for nitrile-functionalized heterocycles. Its high reactivity stems from the electron-deficient double bond, enabling efficient cycloadditions with dienes under mild conditions. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for synthetic workflows requiring precise functional group placement in complex scaffolds.

Synthesis

  • Route1

    References

    • Justus Liebigs Annalen der Chemie, , vol. 551, p. 49
  • Route2
    • null|null
      107-13-1
    • ~%
    • null|null
      928-53-0
    • In-stock
      Fumaronitrile|CS-0022396
      764-42-1

    References

    • Tetrahedron Letters, , vol. 46, # 42 p. 7225 - 7228
  • Route3
    • null|null
      107-13-1
    • ~64%
    • In-stock
      Fumaronitrile|CS-0022396
      764-42-1

    References

    • Ding, Xiong; Lv, Xianhai; Hui, Bin; Chen, Zhijuan; Xiao, Minliang; Guo, Baoshou; Tang, Wenming Tetrahedron Letters, 2006 , vol. 47, # 17 p. 2921 - 2924

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   47.58
  • LogP   1.22586
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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