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2-(3,5,5-Trimethylcyclohex-2-en-1-ylidene)malononitrile

  • CAS No. 23051-44-7

  • Cat. No. CS-0120086
  • Molecule weight186.25
  • Purity≥96%
  • MDL No.MFCD00228058

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

2-(3,5,5-Trimethylcyclohex-2-en-1-ylidene)malononitrile|CS-0120086

Structure of 23051-44-7

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General Information

  • CAS No. 23051-44-7
  • Cat. No. CS-0120086
  • Purity ≥96%
  • MDL No. MFCD00228058
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₄N₂
  • Molecular Weight 186.25
  • Synonym(s) Propanedinitrile, 2-(3,5,5-trimethyl-2-cyclohexen-1-ylidene)-
  • SMILES N#C/C(C#N)=C1C=C(C)CC(C)(C)C/1

Description

This malononitrile derivative features a sterically hindered cyclohexenylidene core that enhances stability and facilitates efficient Michael additions. The electron-deficient double bond enables rapid conjugate addition reactions, making it valuable for synthesizing complex heterocycles under mild conditions.

Application

2-(3,5,5-Trimethylcyclohex-2-en-1-ylidene)malononitrile serves as a versatile Michael acceptor and Diels-Alder dienophile, leveraging its conjugated enone-like system for efficient cycloaddition and nucleophilic addition reactions. Its sterically shielded cyclohexenylidene core enhances bench stability and simplifies purification, while the dual nitrile groups provide high reactivity in heterocycle synthesis and functional group interconversions.

Synthesis

  • Route1
    • In-stock
      Isophorone|CS-0015924
      78-59-1
    • null|null
      109-77-3
    • ~92%
    • In-stock
      2-(3,5,5-Trimethylcyclohex-2-en-1-ylidene)malononitrile|CS-0120086
      23051-44-7

    References

    • Zhang, Xu; Chen, Yi Dyes and Pigments, 2013 , vol. 99, # 3 p. 531 - 536

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H317
Precautionary Statements : P261-P272-P280-P302+P352-P363-P501

Quality Control

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Computational Chemistry Data

  • TPSA   47.58
  • LogP   3.09646
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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