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CS-W001157 4
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2-[bis(methylsulfanyl)methylidene]propanedinitrile

  • CAS No. 5147-80-8

  • Cat. No. CS-0038332
  • Molecule weight170.26
  • Purity≥98%
  • MDL No.None

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

2-[bis(methylsulfanyl)methylidene]propanedinitrile|CS-0038332

Structure of 5147-80-8

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General Information

  • CAS No. 5147-80-8
  • Cat. No. CS-0038332
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆N₂S₂
  • Molecular Weight 170.26
  • Synonym(s) Propanedinitrile, [bis(methylthio)methylene]-
  • SMILES CSC(=C(C#N)C#N)SC

Description

This dinitrile features a bis(methylsulfanyl)methylidene moiety that imparts enhanced solubility and stability under standard conditions. The electron-deficient carbon bridge enables efficient coupling in transition metal-catalyzed transformations, while the terminal nitrile groups serve as robust handles for further functionalization.

Application

2-[Bis(methylsulfanyl)methylidene]propanedinitrile serves as a versatile building block in synthetic organic chemistry, enabling the construction of heterocyclic scaffolds through nucleophilic addition and cyclization reactions. Its dinitrile functionality and thiocarbonyl-stabilized methylene group offer high reactivity toward amines, thiols, and organometallics, facilitating access to functionalized pyrroles, thiazoles, and related frameworks. The molecule exhibits good bench stability and simplifies purification due to its defined polarity and low volatility, making it well-suited for iterative synthesis and process development workflows.

Synthesis

  • Route1
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      75-15-0
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      109-77-3
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      74-88-4
    • ~98%
    • In-stock
      2-[bis(methylsulfanyl)methylidene]propanedinitrile|CS-0038332
      5147-80-8

    References

    • El-Shafei, Ahmed Kamal; Soliman, Ahmed Mohamed; Sultan, Adel Abdel-Rahim; El-Saghier, Ahmed Mohamed Mohamed Gazzetta Chimica Italiana, 1995 , vol. 125, # 3 p. 115 - 118
  • Route2
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      75-15-0
    • null|null
      77-78-1
    • null|null
      109-77-3
    • ~84%
    • In-stock
      2-[bis(methylsulfanyl)methylidene]propanedinitrile|CS-0038332
      5147-80-8

    References

    • Yu, Shen-Yi; Cai, Ya-Xian Synthetic Communications, 2003 , vol. 33, # 22 p. 3989 - 3995
  • Route3
    • null|null
      77-78-1
    • null|null
      109-77-3
    • ~11%
    • In-stock
      2-[bis(methylsulfanyl)methylidene]propanedinitrile|CS-0038332
      5147-80-8

    References

    • Sterling Winthrop Inc. Patent: US5294612 A1, 1994 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302+H312-H315-H319-H331-H335
Precautionary Statements : P261-P280-P305+P351+P338

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Computational Chemistry Data

  • TPSA   47.58
  • LogP   1.97116
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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